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

HRID 1361534Notes

Reaction equation

HRID 1361534 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].[CH3:27][O:28][C:29](=[O:33])[CH2:30][CH2:31][SH:32]>>[CH3:27][O:28][C:29](=[O:33])[CH2:30][CH2:31][S:32][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

3

Reactant 2

HCID 18050Methyl 3-mercaptopropionateHCID 866323843-isopropyloxy-5-phenoxy-N-(5-bromothiazol-2-yl)benzamide

Product 1

HCID 248120843-[2-(3-Isopropoxy-5-phenoxy-benzoylamino)-thiazol-5-yl-sulfanyl]-propionic acid methyl esterYield 7.5%

Procedure

3-[2-(3-Isopropoxy-5-phenoxy-benzoylamino)-thiazol-5-yl-sulfanyl]-propionic acid methyl ester (30 mg) was prepared from 3-isopropyloxy-5-phenoxy-N-(5-bromothiazol-2-yl)benzamide (example 1, step 2) (370 mg, 0.85 mmol) and 3-mercaptopropionic acid methyl ester (0.5 mL, 4.0 mmol) in 7% yield following general procedure F.

Sources & evidence

ORD record
ord-2a5d8c87f93c46cd8f7001f374104af8
Source dataset
uspto-grants-2011_02
Patent number
US07880012B2

Reaction notes

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