Cesium carbonate → tert-Butyl 1-(tert-butoxycarbonyl)-2-(5-tert-butyloxazol-4-yl)vinylcarbamate

HRID 15394Notes

Reaction equation

HRID 15394 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH:7](P(OC)(OC)=O)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:23]([C:27]1[O:31][CH:30]=[N:29][C:28]=1[CH:32]=O)([CH3:26])([CH3:25])[CH3:24].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[C:1]([O:5][C:6]([C:7]([NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:32][C:28]1[N:29]=[CH:30][O:31][C:27]=1[C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 210314885-Tert-butyloxazole-4-carboxaldehydeHCID 58731348N-(tert-Butoxycarbonyl)-alpha-dimethylphosphonoglycine-tert-butyl ester

Product 1

HCID 72404735tert-Butyl 1-(tert-butoxycarbonyl)-2-(5-tert-butyloxazol-4-yl)vinylcarbamateYield 47.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(tert-Butoxycarbonyl)-α-dimethylphosphonoglycine-tert-butyl ester (11.8 g, 34.68 mmol) and 5-tert-butyloxazole-4-carboxaldehyde (6.9 g, 45.08 mmol) in DMF (50 mL) was added Cs2CO3 (12.4 g, 38.15 mmol) under an argon atmosphere at room temperature. The reaction mixture was stirred for 14 h at room temperature. After removal of solvent in vacuo, the residue was dissolved in AcOEt, successively washed with 10% citric acid, 5% NaHCO3 and saturated NaCl for three times, dried over Na2SO4, and concentrated in vacuo. The residual oil was purified by a silica gel column chromatography to yield 6.0 g (47%) of title compound as a white solid: mp 170-172° C.; 1H NMR (300 MHz, CDCl3) δ 7.74 (s, 1H), 6.55 (s, 1H), 1.54 (s, 9H), 1.49 (s, 9H), 1.38 (s, 9H); HRMS (EI): m/z 366.2159 (M+) (calcd for C19H30N2O5: 366.2154).

Workup

  1. customAfter removal of solvent in vacuo
  2. dissolutionthe residue was dissolved in AcOEt
  3. washsuccessively washed with 10% citric acid, 5% NaHCO3 and saturated NaCl for three times
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residual oil was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-9feb1c2a4f554c11bc3b1c564a85d068
Source dataset
uspto-grants-2010_06
Patent number
US07732605B2

Reaction notes

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