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Potassium Hydroxide → Captopril
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Potassium Hydroxide | HCID 14797 | — |
| 反応物 | Sodium Hydroxide | HCID 14798 | — |
| 反応物 | Potassium Phosphate, Tribasic | HCID 62657 | — |
| 反応物 | L-Proline | HCID 145742 | — |
| 反応物 | (S)-1-(3-(Acetylthio)-2-methyl-1-oxopropyl)-L-proline | HCID 689016 | — |
| 反応物 | (R)-3-(Acetylthio)isobutyryl Chloride | HCID 11830043 | — |
| 生成物 | Captopril | HCID 44093 | 67% |
反応手順
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.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05387697 |
| 出典データセット | uspto-grants-1995_02 |
| ORD ID | ord-a4ff7a4be9eb423187ea9252a7975906 |
| 出典メモ | uspto-grants-1995_02 |