Hydrochloric Acid → (S-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acid

HRID 2106915

반응식

HRID 2106915 반응식
[OH:1][C@H:2]([C@H:6]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1)[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14]C(=O)C)[C:3]([OH:5])=[O:4].Cl>O>[OH:1][C@H:2]([C@H:6]([C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14])[C:3]([OH:5])=[O:4]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 57087568HCID 57087568, 화합물

생성물 1

HCID 6451869(S-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acid수율 6.8%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
15 °C

실험 절차

60 g (1.65 mol) of (2S,3S)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-acetylaminophenylthio)propionic acid were suspended in 300 ml of water containing 50 ml of 32% (w/w) hydrochloric acid in the presence of 0.5 g of KI. The mixture was heated to slow reflux for about 3 hours, filtered at about 80° C., separating approximatively 10 g of unsolubles, and the filtered waters were neutralized to pH 6 with 30% (w/w) NaOH, cooled to about 15° C., filtered and thoroughly washed with water. 36 g of (2S,3S)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propionic acid were obtained with 80% optical purity 98-100%. The acid pH hot filtered unsolubles consisted of a mixture of non unhydrolyzed compound and of compound cyclized to benzothiazepine ring.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto slow reflux for about 3 hours
  3. filtrationfiltered at about 80° C.
  4. customseparating approximatively 10 g of unsolubles
  5. filtrationfiltered
  6. washthoroughly washed with water

출처 및 근거

ORD 기록
ord-4c86a9d036724681b045b91d242584ed
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04931587

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