JPS55355A - Preparation of (2s,3r) or (2s,3s)-3-amino-2-hyroxypropionic acid derivative - Google Patents
Preparation of (2s,3r) or (2s,3s)-3-amino-2-hyroxypropionic acid derivativeInfo
- Publication number
- JPS55355A JPS55355A JP2663279A JP2663279A JPS55355A JP S55355 A JPS55355 A JP S55355A JP 2663279 A JP2663279 A JP 2663279A JP 2663279 A JP2663279 A JP 2663279A JP S55355 A JPS55355 A JP S55355A
- Authority
- JP
- Japan
- Prior art keywords
- isomer
- phenyl
- amino
- hyroxypropionic
- preparation
- 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.)
- Granted
Links
- 239000002253 acid Substances 0.000 title abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 2
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 230000003327 cancerostatic effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: Thionyl chloride is made to act on (2R,3R) isomer and (2R,3S) isomer, which are useless because they have no enzyme inhibition activity, and the hydrolysis is effected to produce title compound used for synthetic intermediate of immunologically activated carcinostatics.
CONSTITUTION: Thionyl chloride or sulfonyl chloride is made to act on (2R,3R) or (2R,3S)-3-amino-2-hydroxypropionic ester derivative of the formula [R1 is cycloalkyl, lower alkyl, phenyl, substituted phenyl, benzyl, substituted benzyl; R2 is lower alkyl, phenyl, substituted phenyl; R3 is residue of ester] in such an amount that thionyl chlride or sulfonyl chloride can be used also as the solvent, 5W10 times equivalent at -10W10°C. The resulting product is hydrolyzed with acid or alkali to produce the objective (2S,3R) or (2S,3S) isomer.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2663279A JPS55355A (en) | 1979-03-09 | 1979-03-09 | Preparation of (2s,3r) or (2s,3s)-3-amino-2-hyroxypropionic acid derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2663279A JPS55355A (en) | 1979-03-09 | 1979-03-09 | Preparation of (2s,3r) or (2s,3s)-3-amino-2-hyroxypropionic acid derivative |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53049941 Division |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55355A true JPS55355A (en) | 1980-01-05 |
| JPS62906B2 JPS62906B2 (en) | 1987-01-10 |
Family
ID=12198816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2663279A Granted JPS55355A (en) | 1979-03-09 | 1979-03-09 | Preparation of (2s,3r) or (2s,3s)-3-amino-2-hyroxypropionic acid derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55355A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4517961A (en) * | 1982-11-09 | 1985-05-21 | Bloor Trevor J | Solar water heating apparatus |
| US20120308588A1 (en) * | 2011-05-31 | 2012-12-06 | Theravance, Inc. | Neprilysin inhibitors |
-
1979
- 1979-03-09 JP JP2663279A patent/JPS55355A/en active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4517961A (en) * | 1982-11-09 | 1985-05-21 | Bloor Trevor J | Solar water heating apparatus |
| US20120308588A1 (en) * | 2011-05-31 | 2012-12-06 | Theravance, Inc. | Neprilysin inhibitors |
| US8686184B2 (en) * | 2011-05-31 | 2014-04-01 | Theravance, Inc. | Neprilysin inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62906B2 (en) | 1987-01-10 |
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