4-Methylmorpholine → [(1S,2S)-1-(4-acetyl-thiazol-2-ylcarbamoyl)-2-phenyl-propyl]-carbamic acid tert-butyl ester

HRID 32806Notes

Reaction equation

HRID 32806 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([C:17](F)=[O:18])[C@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2].[NH2:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[O:29])[CH3:28])[N:26]=1.CN1CCOCC1>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:20])[NH:7][C@H:8]([C:17](=[O:18])[NH:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[O:29])[CH3:28])[N:26]=1)[C@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 31119641-(2-Amino-1,3-thiazol-4-yl)ethan-1-oneHCID 86603378HCID 86603378, compound

Product 1

HCID 86603377[(1S,2S)-1-(4-acetyl-thiazol-2-ylcarbamoyl)-2-phenyl-propyl]-carbamic acid tert-butyl esterYield 99.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crude ((1S,2S)-1-fluorocarbonyl-2-phenyl-propyl)-carbamic acid tert-butyl ester (2.2 g, ≈6.93 mol), 1-(2-amino-thiazol-4-yl)-ethanone (1.0 g, 7.0 mmol), 4-methyl morpholine (1.56 mL, 14 mmol) and N,N-dimethylaminopyridine (10 mg, 0.082 mmol) were dissolved in tetrahydrofuran (20 mL). The mixture was microwaved at 120° C. for 15 minutes. The solution was diluted with ethyl acetate and washed with 1.5 M aqueous potassium hydrogen sulfate, water and brine. After drying (sodium sulfate), filtration and evaporation of the solvents, [(1S,2S)-1-(4-acetyl-thiazol-2-ylcarbamoyl)-2-phenyl-propyl]-carbamic acid tert-butyl ester (2.8 g, 89%) was obtained as a yellow foam.

Workup

  1. customThe mixture was microwaved at 120° C. for 15 minutes
  2. washwashed with 1.5 M aqueous potassium hydrogen sulfate, water and brine
  3. customAfter drying
  4. filtration(sodium sulfate), filtration and evaporation of the solvents

Sources & evidence

ORD record
ord-67098673a4c448849a62c8281ba8a3b5
Source dataset
uspto-grants-2008_09
Patent number
US07427635B2

Reaction notes

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