Methyl 3-(4-{4-[1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}benzylsulfanyl)propionate → 2-(4-(4-((1-(2-Chlorophenyl)ethoxy)carbonyl)isoxazol-3-yl)benzylthio)ethanesulfonic acid

HRID 2111009Notes

Reaction equation

HRID 2111009 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(OC)=O)=[CH:21][CH:20]=2)=[N:16][O:17][CH:18]=1)=[O:12])[CH3:9].SCC[S:36]([O-:39])(=[O:38])=[O:37].[Na+]>>[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:20]=[CH:21][C:22]([CH2:23][S:24][CH2:25][CH2:26][S:36]([OH:39])(=[O:38])=[O:37])=[CH:31][CH:32]=2)=[N:16][O:17][CH:18]=1)=[O:12])[CH3:9]

Participants

3

Reactant 2

HCID 11454331Methyl 3-(4-{4-[1-(2-chlorophenyl)ethoxycarbonylamino]-3-isoxazolyl}benzylsulfanyl)propionateHCID 23662354Mesna

Product 1

HCID 113409212-(4-(4-((1-(2-Chlorophenyl)ethoxy)carbonyl)isoxazol-3-yl)benzylthio)ethanesulfonic acidYield 39.3%

Procedure

Reaction similar to that of Step B-7 of Example 1 was carried out using Compound 1 (100 mg, 0.256 mmol) and sodium 2-mercaptoethanesulfonate (127 mg, 0.774 mmol) to give the title compound (50 mg, 39%).

Workup

  1. customReaction similar to that of Step B-7 of Example 1

Sources & evidence

ORD record
ord-5fc552c897d94beab608cc798aa94451
Source dataset
uspto-grants-2009_04
Patent number
US07517996B2

Reaction notes

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