Acetyl chloride → Benzyl (S)-(-)-tetrahydro-5-oxo-3-furanylcarbamate

HRID 1374447

Reaction equation

HRID 1374447 reaction equation
C(Cl)(=O)C.[CH2:5]([O:12][C:13]([NH:15][C@H:16]([CH2:25][OH:26])[CH2:17][C:18]([O:20][C:21](C)(C)[CH3:22])=[O:19])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(O)C>[CH2:5]([O:12][C:13]([NH:15][C@H:16]([CH2:25][OH:26])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:14])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1.[O:20]=[C:18]1[O:26][CH2:25][C@@H:16]([NH:15][C:13](=[O:14])[O:12][CH2:5][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:17]1

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 15043090(S)-tert-Butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxybutanoate

Product 2

HCID 697922Benzyl (S)-(-)-tetrahydro-5-oxo-3-furanylcarbamateYield 56%HCID 57325876ethyl (3S)-3-{[(benzyloxy)carbonyl]amino}-4-hydroxybutanoateYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To ethanol (188 ml, 3.24 mol) was added at 0° C. acetyl chloride (46 ml, 0.65 mol). The mixture was stirred at the same temperature for 30 minutes and added to tert-butyl(3S)-3-{[(benzyloxy)carbonyl]amino}-4-hydroxybutanoate (10.0 g, 32.3 mmol) in ethanol (20 ml). The mixture was stirred overnight. After removal of the solvent, the residue was dissolved in ethyl acetate and the solution was washed with a saturated aqueous sodium hydrogen carbonate solution and then a saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The organic solvent was removed under reduced pressure, and the residue was purified by silica gel chromatography to give ethyl (3S)-3-{[(benzyloxy)carbonyl]amino}-4-hydroxybutanoate (2.92 g, 32%) with a lactone compound, benzyl (3S)-5-oxotetrahydro-3-furanylcarbamate (4.24 g, 56%) as by-product.

Workup

  1. stirringThe mixture was stirred overnight
  2. customAfter removal of the solvent
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washthe solution was washed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate
  6. customThe organic solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-417b2c9ece03475ea8bc35f826a6ae0a
Source dataset
uspto-grants-2007_01
Patent number
US07163936B2

Linked notes

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