Triethylamine → tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

HRID 643060Notes

Reaction equation

HRID 643060 reaction equation
[C:1]([NH:8][C@H:9]([CH2:17][OH:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C>ClCCl.CS(C)=O>[CH2:10]([C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:6])([CH3:5])[CH3:7])[CH:17]=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 2733675tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate

Product 1

HCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamateYield 111.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

(S)—N-Bocphenylalaninol (5 g, 0.019 mol) was dissolved in dichloromethane (150 mL) and triethylamine (8.3 mL, 3 equivalents) at 0° C. and treated with a solution of pyridine-sulfur trioxide complex (9.5 g, 3 equivalents) in DMSO (30 mL) over several minutes. After 1 h at 0° C., the mixture was added to ice water (200 mL). The dichloromethane was evaporated and the mixture was extracted with ether (100 mL, 4×). The organic layer was washed with 10% citric acid, water, saturated sodium bicarbonate, brine, dried over sodium sulfate, and the solvents were evaporated to give 5.3 g of the title compound.

Workup

  1. customThe dichloromethane was evaporated
  2. extractionthe mixture was extracted with ether (100 mL, 4×)
  3. washThe organic layer was washed with 10% citric acid, water, saturated sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvents were evaporated

Sources & evidence

ORD record
ord-d53318beeed1418888a4ac3fd1903216
Source dataset
uspto-grants-2010_04
Patent number
US07696226B2

Reaction notes

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