2-Aminothiazole → 2-Propyl-2-(3-thiazol-2-ylureido)pentanoic acid ethyl ester
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7](N1C=CN=C1)(N1C=CN=C1)=[O:8].[CH2:19]([O:21][C:22](=[O:31])[C:23]([NH2:30])([CH2:27][CH2:28][CH3:29])[CH2:24][CH2:25][CH3:26])[CH3:20]>O1CCCC1>[CH2:19]([O:21][C:22](=[O:31])[C:23]([CH2:27][CH2:28][CH3:29])([NH:30][C:7]([NH:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1)=[O:8])[CH2:24][CH2:25][CH3:26])[CH3:20]Participants
Procedure
A solution of 5.40 g of 2-aminothiazole in 150 ml of tetrahydrofuran was combined at 20° C. with 8.75 g of 1,1'-carbonyldiimidazole and the mixture stirred for 30 minutes. The mixture was then raised within 20 minutes to a bath temperature of between 55 and 60° C. and a solution of 9.80 g of the product from stage 3 in 30 ml of tetrahydrofuran was added dropwise. A clear, red-brown solution was obtained, which was stirred for 60 hours at a temperature of between 55° C. and 60° C. Once the solvent had been removed by distillation, the residue was purified by passage through a silica gel column with ethyl acetate. 10.20 g of 2-propyl-2-(3-thiazol-2-ylureido)pentanoic acid ethyl ester (62% of th.) were obtained in the form of a yellowish oil.
Workup
- temperatureThe mixture was then raised within 20 minutes to a bath temperature of between 55 and 60° C.
- customA clear, red-brown solution was obtained
- stirringwhich was stirred for 60 hours at a temperature of between 55° C. and 60° C
- customOnce the solvent had been removed by distillation
- customthe residue was purified by passage through a silica gel column with ethyl acetate
Sources & evidence
- ORD record
- ord-481ec8cb477d45b29a31d7306e02d62b
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06004963
Reaction notes
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