Methyl Thioglycolate → [2-(3-Isopropoxy-5-phenoxy-benzoylamino)-thiazol-5-yl-sulfanyl]-acetic acid methyl ester

HRID 1361533Notes

Reaction equation

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

Participants

Reactant 2

HCID 16907Methyl Thioglycolate

HCID 866323843-isopropyloxy-5-phenoxy-N-(5-bromothiazol-2-yl)benzamide

Product 1

HCID 17751105[2-(3-Isopropoxy-5-phenoxy-benzoylamino)-thiazol-5-yl-sulfanyl]-acetic acid methyl esterYield 26%

Procedure

[2-(3-Isopropoxy-5-phenoxy-benzoylamino)-thiazol-5-yl-sulfanyl]-acetic acid methyl ester (100 mg) was prepared from 3-isopropyloxy-5-phenoxy-N-(5-bromothiazol-2-yl)-benzamide (370 mg, 0.85 mmol) and methyl mercaptoacetate (0.4 mL, 4.0 mmol) in 26% yield following the general procedure F.

Sources & evidence

ORD record: ord-86559977ea814d8fa1afd39222d10e67
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880012B2

Reaction notes

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