N-Hydroxyphthalimide → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(1H-imidazol-2-ylmethoxyimino)acetic acid

HRID 728591Notes

Reaction equation

HRID 728591 reaction equation
Br[CH2:2][C:3]1[NH:4][CH:5]=[CH:6][N:7]=1.[OH:8][N:9]1C(=O)C2=CC=CC=C2C1=O.[NH2:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=O)[C:27]([OH:29])=[O:28])[N:25]=1>>[NH2:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:9]/[O:8][CH2:2][C:3]2[NH:4][CH:5]=[CH:6][N:7]=2)/[C:27]([OH:29])=[O:28])[N:25]=1

Participants

4

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 127833204-Thiazoleacetic acid, 2-amino-alpha-oxo-HCID 218933732-(Bromomethyl)-1H-imidazole

Product 1

HCID 88527878(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(1H-imidazol-2-ylmethoxyimino)acetic acid

Procedure

N.m.r. in solvent A: 4.15 (m, 1H), 4.38 (m, 1H), 4.48 (m, 1H , 4.92 (m, 1H , 6.94 (s, 1H), 7.4 (s, 15H). 9. N.m.r. in solvent C: 3.4 (m, 2H), 4.2 - 4.6 (m, 4H), 4.7 (m, 1H), 5.0 (m, 1H), 5.1 (d, 1H), 5.9 (d, 1H), 6.9 (s, 1H), 7.4 (s, 15H). 10. The starting material was prepared by reaction of 2-bromomethylimidazole with N-hydroxy-phthalimide, deprotection to give 0-(imidazol-2-yl)methylhydroxylamine and condensation with 2-(2-aminothiazol-4-yl)glyoxylic acid to give 2-(2-aminothiazol-4-yl)-2-[(Z)-(imidazol-2-yl)-methoxyimino]acetic acid.

Workup

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Sources & evidence

ORD record
ord-479f0cd179ea4b598abb81ae1019db12
Source dataset
uspto-grants-1991_09
Patent number
US05049558

Reaction notes

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