Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Potassium Hydroxide → Captopril
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Potassium Hydroxide | HCID 14797 | — |
| 반응물 | Sodium Hydroxide | HCID 14798 | — |
| 반응물 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 반응물 | L-Proline | HCID 145742 | — |
| 반응물 | (S)-1-(3-(Acetylthio)-2-methyl-1-oxopropyl)-L-proline | HCID 689016 | — |
| 반응물 | (R)-3-(Acetylthio)isobutyryl Chloride | HCID 11830043 | — |
| 생성물 | Captopril | HCID 44093 | 67% |
반응 단계
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.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US05387697 |
| 출처 데이터셋 | uspto-grants-1995_02 |
| ORD ID | ord-a4ff7a4be9eb423187ea9252a7975906 |
| 출처 메모 | uspto-grants-1995_02 |