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

HRID 554888Notes

Reaction equation

HRID 554888 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[C@@H:11]([CH3:12])[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.FC1C=CC(CN2[C@H](C)CN(C3SC(C(OCC)=O)=C(C)N=3)C2=O)=CC=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C@H:11]([CH3:12])[CH2:10][N:9]([C:13]3[S:14][C:15]([C:19]([OH:21])=[O:20])=[C:16]([CH3:18])[N:17]=3)[C:8]2=[O:24])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 57919827(R)-ethyl 2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylateHCID 57919865(S)-ethyl 2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate

Product 1

HCID 57919880(R)-2-(3-(4-fluorobenzyl)-4-methyl-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 (R)-ethyl 2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate, the title compound was obtained as a colorless solid (87%): 1H NMR (300 MHz, DMSO-d6) δ 12.85 (s, 1H), 7.40-7.35 (m, 2H), 7.21-7.15 (m, 2H), 4.59 (d, J=15.6 Hz, 1H), 4.30 (d, J=15.6 Hz, 1H), 4.19 (t, J=9.6 Hz, 1H), 4.29-4.14 (m, 1H), 3.78-3.71 (m, 1H), 3.56 (dd, J=10.6, 6.3 Hz, 1H), 2.50 (s, 3H), 1.22 (d, J=6.2 Hz, 3H); MS (ES+) m/z 349.9 (M+1).

Workup

  1. customas described in Preparation 6

Sources & evidence

ORD record
ord-700a8b35c1e9418cb798cc8327ef9d7e
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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