Hydrochloric Acid → (S-(R*,R*))-3-((o-Aminophenyl)thio)-3-(p-methoxyphenyl)lactic acid
Reaction equation
[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]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
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.
Workup
- temperatureThe mixture was heated
- temperatureto slow reflux for about 3 hours
- filtrationfiltered at about 80° C.
- customseparating approximatively 10 g of unsolubles
- filtrationfiltered
- washthoroughly washed with water
Sources & evidence
- ORD record
- ord-4c86a9d036724681b045b91d242584ed
- Source dataset
- uspto-grants-1990_06
- Patent number
- US04931587
Reaction notes
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