Potassium Hydroxide → Captopril

HRID 273893

反応式

HRID 273893 の反応式
N1CCC[C@H]1C(O)=O.C(SC[C@@H](C)C(Cl)=O)(=O)C.[OH-].[K+].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C([S:32][CH2:33][C@@H:34]([CH3:45])[C:35]([N:37]1[CH2:44][CH2:43][CH2:42][C@H:38]1[C:39]([OH:41])=[O:40])=[O:36])(=O)C.[OH-].[Na+]>>[CH3:45][C@@H:34]([C:35]([N:37]1[C@H:38]([C:39]([OH:41])=[O:40])[CH2:42][CH2:43][CH2:44]1)=[O:36])[CH2:33][SH:32]

参加物

7

反応物 6

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 145742L-Proline3 回HCID 689016(S)-1-(3-(Acetylthio)-2-methyl-1-oxopropyl)-L-prolineHCID 11830043(R)-3-(Acetylthio)isobutyryl Chloride

生成物 1

HCID 44093Captopril収率 67%

実験手順

It has been found that the compound of the formula I can be prepared from L-proline in two reaction steps with a total yield of 67% through the acylation of L-proline, if L-proline is acylated with (R)-3-acetylthio-2-methylpropanoyl chloride of formula III: ##STR3## in the presence of KOH and potassium phosphate buffer at pH 7.5-8.5, and at a temperature of between about 0°-5° C. The resulting compound is 1-[3-acetylthio-2-(S)-methylpropanoyl]-L-proline, ##STR4## Compound IV, which also can be termed "S-acetyl captopril", can be acidified and then deblocked with sodium hydroxide to give captopril in yield of 67% relative to starting material of formula III, without any unwanted byproducts.

後処理

  1. customof between about 0°-5° C

出典と根拠

ORDレコード
ord-a4ff7a4be9eb423187ea9252a7975906
出典データセット
uspto-grants-1995_02
特許番号
US05387697

関連ノート

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