Chloroacetone → Tert-butyl 1-(4-methylthiazol-2-yl)ethylcarbamate

HRID 1784927Notes

Reaction equation

HRID 1784927 reaction equation
[C:1]([NH:8][C@H:9]([C:11](=[S:13])[NH2:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl[CH2:15][C:16](=O)[CH3:17].C(=O)([O-])[O-].[Ca+2]>C(O)C>[CH3:17][C:16]1[N:12]=[C:11]([CH:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:5])[CH3:6])[CH3:10])[S:13][CH:15]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 10112Calcium CarbonateHCID 10932591tert-butyl N-[(1S)-1-carbamothioylethyl]carbamate

Product 1

HCID 57513079Tert-butyl 1-(4-methylthiazol-2-yl)ethylcarbamateYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of BOC-alanine-thioamide (1.39 g, 6.81 mmoles), chloroacetone (0.65 mL, 8.18 mmoles) and calcium carbonate (1.0 g, 10.22 mmoles) were refluxed in ethanol (25 mL) for 4 h. The reaction was cooled to room temperature and quenched with 2OmL of saturated aq. NaHCO3 solution. Ethanol was evaporated under reduced pressure and extracted with ethyl acetate (2×30 mL). The combined organic layers was dried over Na2SO4 and concentrated. The residue was chromatographed on silica gel (20% ethyl acetate/80% hexane) to yield 48% of the desired product.

Workup

  1. customquenched with 2OmL of saturated aq. NaHCO3 solution
  2. customEthanol was evaporated under reduced pressure
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. dry with materialThe combined organic layers was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel (20% ethyl acetate/80% hexane)

Sources & evidence

ORD record
ord-8fda7e41797e40d284ad385eb199a360
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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