Chloroacetone → tert-butyl [(1R)-1-(4-methyl-1,3-thiazol-2-yl)ethyl]carbamate
Reaction equation
[NH2:1][C:2](=[S:13])[C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].Cl[CH2:15][C:16](=O)[CH3:17]>C(O)C>[CH3:17][C:16]1[N:1]=[C:2]([C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[CH3:4])[S:13][CH:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of tert-butyl [(1R)-2-amino-1-methyl-2-thioxoethyl]carbamate (100 mg, 0.49 mmol) with 3 equivalents of chloroacetone (0.135 g) in ethanol (1 mL) was heated at 80° C. for 2 h. After cooling, the solution was concentrated. The residue was dissolved in DCM (1 ml). To the solution was added TFA (1 mL). The mixture was stirred at RT for 30 min. The volatiles were removed under reduced pressure to yield desired product.
Workup
- temperatureAfter cooling
- concentrationthe solution was concentrated
- dissolutionThe residue was dissolved in DCM (1 ml)
- additionTo the solution was added TFA (1 mL)
- customThe volatiles were removed under reduced pressure
Sources & evidence
- ORD record
- ord-2597db653cc7489294c9a999e7daec91
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683060B2
Reaction notes
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