Hexane → methyl 3-(4-{4-[(1R)-1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}benzylsulfanyl)propionate

HRID 2111006Notes

Reaction equation

HRID 2111006 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([O:10][C:11]([NH:13][C:14]1[C:15]([C:19]2[CH:32]=[CH:31][C:22]([CH2:23][S:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)=[N:16][O:17][CH:18]=1)=[O:12])[CH3:9].CCCCCC>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]([O:10][C:11]([NH:13][C:14]1[C:15]([C:19]2[CH:32]=[CH:31][C:22]([CH2:23][S:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:21][CH:20]=2)=[N:16][O:17][CH:18]=1)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 8058HexaneHCID 11454331Methyl 3-(4-{4-[1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}benzylsulfanyl)propionate

Product 1

HCID 68880145methyl 3-(4-{4-[(1R)-1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}benzylsulfanyl)propionateYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3-(4-{4-[1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}benzylsulfanyl)propionate (110 mg, 0.232 mmol) was subjected to optical resolution by high performance liquid chromatography (HPLC) (hexane:ethanol=8:2) using CHIRALCEL OD column (2 cm I.D.×25 cm L; DAICEL CHEMICAL IND., LTD) to give the title compound (R form, 54 mg, 49%) along with its S form (55 mg, 50%). The optical purity was determined by HPLC analysis using an optically active column.

Sources & evidence

ORD record
ord-b097c3dd53c24ac88d7f6b7ab6aceafe
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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