JPH04208257A - Production of optically active 3-amino-4-cyclohexyl-2--hydroxybutyric acid ester hydrochloride - Google Patents
Production of optically active 3-amino-4-cyclohexyl-2--hydroxybutyric acid ester hydrochlorideInfo
- Publication number
- JPH04208257A JPH04208257A JP2307230A JP30723090A JPH04208257A JP H04208257 A JPH04208257 A JP H04208257A JP 2307230 A JP2307230 A JP 2307230A JP 30723090 A JP30723090 A JP 30723090A JP H04208257 A JPH04208257 A JP H04208257A
- Authority
- JP
- Japan
- Prior art keywords
- amino
- optically active
- formula
- configuration
- hydroxybutyric acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000002148 esters Chemical class 0.000 title abstract description 3
- LQHZTNXHEVLTBR-UHFFFAOYSA-N 3-amino-4-cyclohexyl-2-hydroxybutanoic acid Chemical compound OC(=O)C(O)C(N)CC1CCCCC1 LQHZTNXHEVLTBR-UHFFFAOYSA-N 0.000 title description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- LDSJMFGYNFIFRK-UHFFFAOYSA-N 3-azaniumyl-2-hydroxy-4-phenylbutanoate Chemical compound OC(=O)C(O)C(N)CC1=CC=CC=C1 LDSJMFGYNFIFRK-UHFFFAOYSA-N 0.000 claims abstract description 4
- AFENDNXGAFYKQO-UHFFFAOYSA-N 2-hydroxybutyric acid Chemical class CCC(O)C(O)=O AFENDNXGAFYKQO-UHFFFAOYSA-N 0.000 claims description 4
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 3
- 239000003054 catalyst Substances 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000002461 renin inhibitor Substances 0.000 abstract description 3
- 229940086526 renin-inhibitors Drugs 0.000 abstract description 3
- 229910052703 rhodium Inorganic materials 0.000 abstract description 3
- 239000010948 rhodium Substances 0.000 abstract description 3
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- 229910052697 platinum Inorganic materials 0.000 abstract description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 abstract description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- -1 3-amino-4-cyclohexyl-2-hydroxybutyric acid ester Chemical class 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- FFOPEPMHKILNIT-UHFFFAOYSA-N Isopropyl butyrate Chemical compound CCCC(=O)OC(C)C FFOPEPMHKILNIT-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- LDSJMFGYNFIFRK-DTWKUNHWSA-N (2r,3s)-3-azaniumyl-2-hydroxy-4-phenylbutanoate Chemical compound OC(=O)[C@H](O)[C@@H](N)CC1=CC=CC=C1 LDSJMFGYNFIFRK-DTWKUNHWSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- RPNNPZHFJPXFQS-UHFFFAOYSA-N methane;rhodium Chemical compound C.[Rh] RPNNPZHFJPXFQS-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は各種レニンインヒビターの中間体として期待さ
れる光学活性３−アミノ−４−シクロへキシル−２−ヒ
ドロキシ酪酸エステル・塩酸塩の新規製造法に関する。[Detailed Description of the Invention] [Industrial Application Field] The present invention is directed to the novel production of optically active 3-amino-4-cyclohexyl-2-hydroxybutyric acid ester/hydrochloride, which is expected to be an intermediate for various renin inhibitors. Regarding the law.
光学活性３−アミノ−４−シクロへキシル−２−ヒドロ
キシ酪酸エステル類を製造する方法としては特開昭６２
−３３１４１及び特開昭６２−２３４０７１か既に知ら
れている。A method for producing optically active 3-amino-4-cyclohexyl-2-hydroxybutyric acid esters is disclosed in JP-A-62
-33141 and JP-A-62-234071 are already known.
前記の方法は原料が高価であり、しかも純度的にも高い
ものか得られない等の欠点かあり満足すべき製法とは言
い難い。The above-mentioned method cannot be called a satisfactory production method because the raw materials are expensive and it cannot be obtained with high purity.
本発明は式（Ｉ）
（式中Ｒはイソプロピル基、（＊）はＳ配置又はＲ配置
を、（＊＊）はＳ配置又はＲ配置を示す）。The present invention relates to formula (I) (wherein R is an isopropyl group, (*) represents S configuration or R configuration, and (**) represents S configuration or R configuration).
て表わされる光学活性３−アミノ−４−フェニル−２−
ヒドロキシ酪酸エステル類を溶媒中で接触還元すること
を特徴とする。Optically active 3-amino-4-phenyl-2-
It is characterized by catalytic reduction of hydroxybutyric acid esters in a solvent.
式（ＩＩ）
Ｈ
（式中Ｒ，（＊）、（＊＊）は前記と同し）で示される
光学活性３−アミノ−４−シクロへキシル−２−ヒドロ
キシ酪酸エステル類の製造法及び上記式（Ｉ）で表わさ
れる光学活性３−アミノ−４−フェニル−２−ヒドロキ
シ酪酸エステル類に関する。Method for producing optically active 3-amino-4-cyclohexyl-2-hydroxybutyric acid esters represented by formula (II) H (wherein R, (*), and (**) are the same as above) and the above The present invention relates to optically active 3-amino-4-phenyl-2-hydroxybutyric acid esters represented by formula (I).
上記式（Ｉ）、（ＩＩ）におけるＲとしては、例えば、
イソプロピル基かあげられる。As R in the above formulas (I) and (II), for example,
An example is the isopropyl group.
本発明において用いられる溶媒としては、例えばメタノ
ール、エタノール、プロパツール、イソプロパツール、
ブタノール、ペンタノールなとの０１〜Ｃ５のアルコー
ルか好ましく、エステル交換反応を考慮すると、エステ
ル基に対応するアルコールを用いるのかよい。Examples of the solvent used in the present invention include methanol, ethanol, propatool, isopropateol,
Alcohols of 01 to C5 such as butanol and pentanol are preferable, and in consideration of transesterification, it is preferable to use alcohols corresponding to ester groups.
接触還元反応に用いられる触媒としては、例えば酸化白
金等の白金系の触媒やロジウム−炭素、ロジウム−アル
ミナなとのロジウム系の触媒か好ましく、その使用量は
式（Ｉ）の化合物に対し３−１５ｗｔ／ｗｔ％好ましく
は５−１０ｗ ｔ ／ ｗ ｔ％程度かよい。The catalyst used in the catalytic reduction reaction is preferably a platinum-based catalyst such as platinum oxide, or a rhodium-based catalyst such as rhodium-carbon or rhodium-alumina, and the amount used is 3% relative to the compound of formula (I). -15 wt/wt%, preferably about 5-10 wt/wt%.
反応温度は特に限定しないか通常２０〜１１０°Ｃ程度
好ましくは５０〜６０°Ｃの温度範囲で行なうのか良い
。The reaction temperature is not particularly limited and may be carried out generally in the range of 20 to 110°C, preferably 50 to 60°C.
水素圧力は特に限定するのものはないか工業的製法を考
慮すると３〜９．５ ｋｇ ／ ｃｒｌ好ましくは５〜
９ ｋｇ ／ ｃイか良い。Is there any particular limit to the hydrogen pressure? Considering industrial production methods, it should be 3 to 9.5 kg/crl, preferably 5 to 5.
9 kg/c is good.
反応終了後、触媒を濾去し、次いて溶媒を留去した後、
再結晶法等により目的物を得ることかてきる。After the reaction was completed, the catalyst was filtered off, and then the solvent was distilled off.
The desired product can be obtained by a recrystallization method or the like.
なお、原料である式（Ｉ）の化合物は、例えは特公昭５
７−５８３３８号記載の光学活性３−アミノ−４−フェ
ニル−２−ヒドロキシ酪酸を酸触媒の存在下、各種アル
コール類と反応させることにより高収率て得ることがて
きる。In addition, the compound of formula (I) which is a raw material is, for example,
The optically active 3-amino-4-phenyl-2-hydroxybutyric acid described in No. 7-58338 can be obtained in high yield by reacting it with various alcohols in the presence of an acid catalyst.
実施例１゜
酸塩
（２Ｒ，３Ｓ）−３−アミノ−４−フェニル−２−ヒド
ロキシ酪酸１５ｇをイソプロパツール２００ ｍｌに懸
濁し、５〜１０°Ｃに保ち、塩化チオニル６、１ ｍｌ
を３０分て加える。その後徐々に温度を上げ５０〜５５
°Ｃで１時間保つ。次いで反応液を減圧濃縮して、イソ
プロパツールを除去し、濃縮残渣に酢酸イソプロピル１
５０ ｍｌを加える。析出する白色結晶を濾別し、酪酸
イソプロピル２０ｍ１で洗浄後乾燥して（２Ｒ，３Ｓ）
−３−アミノ−４−フェニル−２−ヒトロキシ酪酸イソ
プロピルエステル塩酸塩１９．３ ｇ（収率９０．３％
）得た。Example 1 15 g of acid salt (2R,3S)-3-amino-4-phenyl-2-hydroxybutyric acid was suspended in 200 ml of isopropanol, kept at 5-10°C, and 1 ml of thionyl chloride 6.
Add after 30 minutes. Then gradually increase the temperature to 50-55
Keep at °C for 1 hour. The reaction solution was then concentrated under reduced pressure to remove isopropanol, and the concentrated residue was diluted with 1 portion of isopropyl acetate.
Add 50 ml. The precipitated white crystals were separated by filtration, washed with 20 ml of isopropyl butyrate, and dried (2R, 3S).
-3-amino-4-phenyl-2-hydroxybutyric acid isopropyl ester hydrochloride 19.3 g (yield 90.3%)
)Obtained.
融 点 １４８ 〜１４９ ℃〔α）％０−１
３．２° （Ｃ＝２．’４ Ｎ２０）Ｒｆ ０．６
８ （ｎ−ＢｕＯＨ：ＡＣＯＨ：Ｎ２０：４：１：
５）ＮＭＲ（ＣＤ３０Ｄ）
δ１．２〜１．３ （ｍ、 ６Ｈ）
３．０〜３．１ （ｍ、 ２Ｈ）
３、７〜３．８５ （ｍ、 Ｉ Ｈ）４．０５ （ｄ
、ＩＨ）
５、０〜５．１５ （ｍ、 Ｉ Ｈ）７．２５〜７．
４５ （ｍ、５Ｈ）
実施例２゜
チル塩酸塩
（２Ｒ，３Ｓ）−３−アミノ−４−フェニル−２−ヒド
ロキシ酪酸イソプロピルエステル塩酸塩１２．２ｇ、イ
ソプロパツール１２０ｍＬ５％Ｒｈ／ｃ（５０％重量ｗ
ｅｔ）２．４ ｇを５００ ｍｅオートクレーブに加え
、Ｎ２圧２ ｋｇ ／ ｃイで４回、Ｈ２圧２ ｋｇ
／ ｃｎｆて１回、それぞれガス置換してから、Ｈ２圧
７−９ ｋｇ ／ ｃｒ＆を保ち、５０〜６０°Ｃで２
時間水添した。Melting point 148 ~ 149 ℃ [α)%0-1
3.2° (C=2.'4 N20) Rf 0.6
8 (n-BuOH:ACOH:N20:4:1:
5) NMR (CD30D) δ1.2-1.3 (m, 6H) 3.0-3.1 (m, 2H) 3,7-3.85 (m, IH) 4.05 (d
, IH) 5, 0-5.15 (m, IH) 7.25-7.
45 (m, 5H) Example 2 Dethyl hydrochloride (2R,3S)-3-amino-4-phenyl-2-hydroxybutyric acid isopropyl ester hydrochloride 12.2 g, isopropanol 120 mL 5% Rh/c (50% Weight lol
et) 2.4 g was added to a 500 m autoclave, and then 4 times with N2 pressure of 2 kg/c and H2 pressure of 2 kg
/cnf and gas exchange once each, then maintain H2 pressure 7-9 kg/cr& and heat at 50-60 °C for 2 hours.
Hydrogenated for an hour.
次いてこの反応液を濾別し触媒を除いたのち、減圧濃縮
して、イソプロパツールを除去し、濃縮残渣に酢酸イソ
プロピル１５０ｍ１を加える。The reaction solution was then filtered to remove the catalyst, concentrated under reduced pressure to remove isopropanol, and 150 ml of isopropyl acetate was added to the concentrated residue.
析出する白色結晶と濾別し、酢酸イソプロピル２０ｍ１
で洗浄後真空乾燥して、（２Ｒ，３Ｓ）−３−アミノ−
４−シクロへキシル−２−ヒドロキシ酪酸イソプロピル
エステル塩酸塩１１．４ｇ（収率９１．５％）得た。Separate the precipitated white crystals by filtration and add 20ml of isopropyl acetate.
(2R,3S)-3-amino-
11.4 g (yield 91.5%) of 4-cyclohexyl-2-hydroxybutyric acid isopropyl ester hydrochloride was obtained.
〔α） ％６ ９．６° （Ｃ＝２．５ Ｎ２０）
融 点 １１９−１２０ °Ｃ〔効 果〕
本発明によれば、アミノ基を保護する必要はなくエステ
ル化したあとて核還元をおこなうので触媒使用量の低減
にもつながる。しかも品質も良く、高収率で得られ、更
に得られた目的物質はそのままペプチド誘導体の原料と
なるなど、経済性、操作性の点て極めて効率的であり、
工業的製法として適している。[α) %6 9.6° (C=2.5 N20)
Melting point: 119-120°C [Effects] According to the present invention, there is no need to protect the amino group, and nuclear reduction is performed after esterification, which also leads to a reduction in the amount of catalyst used. In addition, it is of good quality and can be obtained in high yield, and the target substance obtained can be used as a raw material for peptide derivatives, making it extremely efficient in terms of economy and operability.
Suitable as an industrial manufacturing method.
なお、本発明方法により得られる式（ｎ）の化合物は例
えば、特開平１−１７２３６５号開示の方法によりレニ
ンインヒビターを得ることかできる。The compound of formula (n) obtained by the method of the present invention can be used to obtain a renin inhibitor, for example, by the method disclosed in JP-A-1-172365.
Claims (2)
を、（＊＊）はＳ配置又はＲ配置を示す。） で表わされる光学活性３−アミノ−４−フェニル−２−
ヒドロキシ酪酸エステル類を溶媒中で接触還元すること
を特徴とする。 式（II） ▲数式、化学式、表等があります▼（II） （式中Ｒ、（＊）、（＊＊）は前記と同じ）で示される
光学活性３−アミノ−４−シクロヘキシル−２−ヒドロ
キシ酪酸エステル類の製造法(1) Formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R is isopropyl group, (*) represents S configuration or R configuration, (**) represents S configuration or R configuration ) Optically active 3-amino-4-phenyl-2-
It is characterized by catalytic reduction of hydroxybutyric acid esters in a solvent. Formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) Optically active 3-amino-4-cyclohexyl-2- represented by (in the formula, R, (*), and (**) are the same as above) Production method of hydroxybutyric acid esters
を、（＊＊）はＳ配置又はＲ配置を示す。） で表わされる光学活性３−アミノ−４−フェニル−２−
ヒドロキシ酪酸エステル類(2) Formula (I) ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) (In the formula, R is isopropyl group, (*) represents S configuration or R configuration, (**) represents S configuration or R configuration ) Optically active 3-amino-4-phenyl-2-
Hydroxybutyrate esters
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2-248747 | 1990-09-20 | ||
| JP24874790 | 1990-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04208257A true JPH04208257A (en) | 1992-07-29 |
Family
ID=17182769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2307230A Pending JPH04208257A (en) | 1990-09-20 | 1990-11-15 | Production of optically active 3-amino-4-cyclohexyl-2--hydroxybutyric acid ester hydrochloride |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04208257A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1238700A1 (en) * | 2001-03-06 | 2002-09-11 | N.E. Chemcat Corporation | Hydrogenolysis catalyst |
-
1990
- 1990-11-15 JP JP2307230A patent/JPH04208257A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1238700A1 (en) * | 2001-03-06 | 2002-09-11 | N.E. Chemcat Corporation | Hydrogenolysis catalyst |
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