Phenyl chloroformate → (5-Cyclobutyl-thiazol-2-yl)-carbamic acid phenyl ester
Reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH:7]2[CH2:10][CH2:9][CH2:8]2)=[CH:5][N:6]=1.C(N(C(C)C)CC)(C)C.[C:20]1([O:26][C:27](Cl)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[C:20]1([O:26][C:27](=[O:28])[NH:1][C:2]2[S:3][C:4]([CH:7]3[CH2:10][CH2:9][CH2:8]3)=[CH:5][N:6]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
5
Conditions
- Temperature
- 23 °C
Procedure
A solution of 2-amino-5-cyclobutyl thiazole (Preparation 2; 2.5 g, 1 6 mmol) and diisopropylethylamine (2.82 mL, 16 mmol) in methylene chloride (200 mL) was cooled to −78° C. and phenylchloroformate (2 mL, 16 mmol) was added dropwise. The reaction mixture was slowly warmed to 23° C., was stirred for 1 hour at this temperature, than was washed with aqueous saturated sodium bicarbonate (2 times) and brine (1 time), was dried (MgSO4), was filtered, and was concentrated in vacuo. The resulting white solid was purified by silica gel chromatography (5:1 CHCl3-hexanes) to afford 3.5 g of the title compound as a white solid.
Workup
- washthan was washed with aqueous saturated sodium bicarbonate (2 times) and brine (1 time)
- dry with materialwas dried (MgSO4)
- filtrationwas filtered
- concentrationwas concentrated in vacuo
- customThe resulting white solid was purified by silica gel chromatography (5:1 CHCl3-hexanes)
Sources & evidence
- ORD record
- ord-99c4c315a6e744d4bdd595e165924c06
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06720427B2
Reaction notes
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