Chloroacetone → tert-butyl [(1R)-1-(4-methyl-1,3-thiazol-2-yl)ethyl]carbamate

HRID 607617

Reaction equation

HRID 607617 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]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 5324342tert-butyl [(1R)-2-amino-1-methyl-2-thioxoethyl]carbamate

Product 1

HCID 59216334tert-butyl [(1R)-1-(4-methyl-1,3-thiazol-2-yl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. temperatureAfter cooling
  2. concentrationthe solution was concentrated
  3. dissolutionThe residue was dissolved in DCM (1 ml)
  4. additionTo the solution was added TFA (1 mL)
  5. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-4fefd6104feb46b1a8729669818232bf
Source dataset
uspto-grants-2011_03
Patent number
US07915408B2

Linked notes

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