Acetic Acid → HCID 57883837, compound
Reaction equation
[CH:1]1([NH:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:14]([O:16][C:17](=[O:25])[CH2:18][C:19]1[N:20]=[C:21]([NH2:24])[S:22][CH:23]=1)[CH3:15].[Br:26]N1[C:31](=[O:32])CCC1=O.[C:34]([OH:37])(=O)C>>[CH2:14]([O:16][C:17](=[O:25])[CH2:18][C:19]1[N:20]=[C:21]([NH:24][C:31]([N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[O:32])[S:22][CH:23]=1)[CH3:15].[CH2:14]([O:16][C:17](=[O:25])[CH2:18][C:19]1[N:20]=[C:21]([NH:24][C:34]([N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:8]2[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]2)=[O:37])[S:22][C:23]=1[Br:26])[CH3:15]Participants
6
Procedure
[2-(3,3-Dicyclohexyl-ureido)-thiazol-4-yl]acetic acid ethyl ester was prepared from dicyclohexylamine and (2-amino-4-thiazolyl)acetic acid ethyl ester as described in general procedure (A). To this compound was added 1.3 equivalents of N-bromosuccinimide suspended in acetic acid, and the mixture was stirred for 3 h at RT. The reaction mixture was concentrated in vacuo, redissolved in dichloromethane, washed with 10% sodium sulphate, water, aqueous sodium bicarbonate, brine and then dried over magnesium sulphate. Flash chromatography afforded the title compound.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutionredissolved in dichloromethane
- washwashed with 10% sodium sulphate, water, aqueous sodium bicarbonate, brine
- dry with materialdried over magnesium sulphate
Sources & evidence
- ORD record
- ord-397c89ad1c794030a83657f7b1aaf78a
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263634B2
Reaction notes
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