(S)-ethyl 2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate → 2-(3-(But-3-enyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

HRID 554887Notes

Reaction equation

HRID 554887 reaction equation
FC1C=C[C:5]([CH2:6][N:7]2[C@@H:11](C)[CH2:10][N:9]([C:13]3[S:14][C:15]([C:19]([O:21]CC)=[O:20])=[C:16]([CH3:18])[N:17]=3)[C:8]2=[O:24])=[CH:4][CH:3]=1.C(N1CCN(C2SC(C(OCC)=O)=C(C)N=2)C1=O)CC=C>>[CH2:6]([N:7]1[CH2:11][CH2:10][N:9]([C:13]2[S:14][C:15]([C:19]([OH:21])=[O:20])=[C:16]([CH3:18])[N:17]=2)[C:8]1=[O:24])[CH2:5][CH:4]=[CH2:3]

Participants

3

Reactant 2

HCID 57919865(S)-ethyl 2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateHCID 57919868Ethyl 2-(3-(but-3-enyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 579200082-(3-(But-3-enyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Procedure

Following the procedure as described in Preparation 6, making variations as required to replace (S)-ethyl 2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate with ethyl 2-(3-(but-3-enyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained as a colourless solid (85%): mp 205-207° C.; 1H NMR (300 MHz, DMSO-d6) δ 12.70 (s, 1H), 5.86-5.72 (m, 1H), 5.16-5.02 (m, 2H), 4.01-3.96 (m, 2H), 3.60-3.54 (m, 2H), 3.31 (t, J=7.1 Hz, 2H), 2.50 (s, 3H), 2.32-2.26 (m, 2H); MS (ES+) m/z 281.8 (M+1).

Workup

  1. customas described in Preparation 6

Sources & evidence

ORD record
ord-c2960715702249a7a9bc9c5a2e798bd3
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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