Hydrogen Sulfide → 2-(4-Boc-aminophenyl)-thiazole-4-carboxylic acid

HRID 460180Notes

Reaction equation

NS(C1C=CC(C2[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])N=2)=CC=1)(=O)=O.[CH3:19][C:20]([CH3:34])([O:22][C:23]([C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[C:27]([NH2:33])[CH:26]=1)=[O:24])[CH3:21].S.BrCC(=O)C(OCC)=O>>[C:23]([C:25]1[CH:32]=[CH:31][C:28]([C:29]2[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:30]=2)=[C:27]([NH2:33])[CH:26]=1)([O:22][C:20]([CH3:34])([CH3:19])[CH3:21])=[O:24]

Participants

Reactant 4

HCID 402Hydrogen Sulfide

HCID 66144Ethyl bromopyruvate

HCID 18771825Tert-butyl 3-amino-4-cyanobenzoate

HCID 187720852-(p-Sulfamoylphenyl)thiazole-4-carboxylic acid

Product 1

HCID 694125982-(4-Boc-aminophenyl)-thiazole-4-carboxylic acid

Procedure

In a manner similar to that described for the preparation of 2-(4-aminosulfonylphenyl)thiazole-4-carboxylic acid, 4-[(1,1-dimethylethoxy)carbonyl]-aminobenzonitrile was treated with H2S, ethyl bromopyruvate, and LIOH successively to give the title compound. MS m/z: 321 (M+H).

Sources & evidence

ORD record: ord-6d9336aac5ce49a0b258eeea0dad86be
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196104B2

Reaction notes

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