Dichloromethane ethylacetate → 3-phenyl-3-{[3'-(1,3-thiazol-2-ylamino)[1,1'-biphenyl]-3-yl]sulfonylamino}-propanoic Acid

HRID 10950

Reaction equation

HRID 10950 reaction equation
[C:1]1([CH:7]([NH:14][S:15]([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]4[S:32][CH:33]=[CH:34][N:35]=4)[CH:25]=3)[CH:21]=[CH:22][CH:23]=2)(=[O:17])=[O:16])[CH2:8][C:9]([O:11]CC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClCCl.C(OC(=O)C)C>C(COC)OC.[Li+].[OH-]>[C:1]1([CH:7]([NH:14][S:15]([C:18]2[CH:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]4[S:32][CH:33]=[CH:34][N:35]=4)[CH:25]=3)[CH:21]=[CH:22][CH:23]=2)(=[O:16])=[O:17])[CH2:8][C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 21226138Dichloromethane ethylacetateHCID 21982424Ethyl 3-phenyl-3-{[3'-(1,3-thiazol-2-ylamino)[1,1'-biphenyl]-3-yl]sulfonylamino}-propanoate

Product 1

HCID 219824973-phenyl-3-{[3'-(1,3-thiazol-2-ylamino)[1,1'-biphenyl]-3-yl]sulfonylamino}-propanoic Acid

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

0.2 g of Ethyl 3-phenyl-3-{[3′-(1,3-thiazol-2-ylamino)[1,1′-biphenyl]-3-yl]sulfonylamino}-propanoate 15.1.1 were saponified in 15 ml dimethoxyethane 12 ml water and 0.2 g LiOH. After aqueos work-up and flash chromatography (dichloromethane/methanol 10+1) 65 mg were obtained.

Sources & evidence

ORD record
ord-d92c58b0faca44eeb43c64c494c5501b
Source dataset
uspto-grants-2006_08
Patent number
US07094911B2

Linked notes

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