Hydrochloric Acid → HCID 15614285, compound
Reaction equation
C[O:2][C:3](=[O:24])[C@H:4]([OH:23])[C@H:5]([C:10](=[O:22])[C@H:11]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[CH:12]([CH3:14])[CH3:13])[C:6]([O:8]C)=[O:7].COCCOC.Cl>O>[OH:23][C@H:4]([C@H:5]([C:10](=[O:22])[C@H:11]([C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)[CH:12]([CH3:14])[CH3:13])[C:6]([OH:8])=[O:7])[C:3]([OH:24])=[O:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 2(R)-hydroxy-3(R)-[2(S)-(4-chlorophenyl)-3-methylbutanoyl]-butanedioic acid dimethyl ester (diastereoisomer K) (1 g, 2.6 mmol), 1,2-dimethoxyethane (18.3 ml) and of conc HCl (18.3 ml) was heated, under stirring, at 70° C. for 1 hour. The reaction mixture was cooled at room temperature, poured into water (50 ml) and extracted with dichloromethane (2×50 ml). The organic phase was extracted with a 10% aqueous solution of sodium bicarbonate (4×50 ml). The aqueous phase was acidified with conc HCl to pH 1 and extracted with dichloromethane (3×50 ml). The combined organic phase was washed with water, anhydrified over sodium sulfate, filtered, and concentrated in vacuo.
Workup
- temperatureThe reaction mixture was cooled at room temperature
- extractionextracted with dichloromethane (2×50 ml)
- extractionThe organic phase was extracted with a 10% aqueous solution of sodium bicarbonate (4×50 ml)
- extractionextracted with dichloromethane (3×50 ml)
- washThe combined organic phase was washed with water
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-af2dce9907624ca289317bc2a2cad6b3
- Source dataset
- uspto-grants-1989_03
- Patent number
- US04810819
Reaction notes
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