Methyl iodide → methyl (2R)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoate

HRID 989518Notes

Reaction equation

HRID 989518 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:19]([OH:21])=[O:20])[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22](=O)(O)[O-].[Na+].CI>CN(C)C=O>[CH3:22][O:20][C:19](=[O:21])[C@@H:9]([CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 2733693(R)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Product 1

HCID 54103156methyl (2R)-3-(benzyloxy)-2-{[(tert-butoxy)carbonyl]amino}propanoateYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of t-butyloxycarbonyl-O-benzyl-D-serine (25.0 g, 84.7 mmol) stirring in dimethylformamide (500 mL) at room temperature was added sodium bicarbonate (14.2 g, 169 mmol) followed by methyl iodide (26.4 mL, 424 mmol). After 18 h, the reaction mixture was concentrated to approximately 100 mL. Ethyl acetate was added and the mixture washed with aqueous sodium bicarbonate and brine. The organic extract was dried and concentrated to give the desired compound (25 g, 96%) as a light yellow oil: 1H NMR (300 MHz, CDCl3) d 1.45 (s, 9H), 3.70 (m, 1H), 3.75 (s, 3H), 3.85 (m, 1H), 4.50 (m, 3H), 7.30 (m, 5H); MS (FD) m/e 310; Anal. calc'd for C16H23NO5: C, 62.12; H, 7.49; N, 4.53. Found: C, 62.31; H, 7.49; N, 4.43.

Workup

  1. concentrationthe reaction mixture was concentrated to approximately 100 mL
  2. additionEthyl acetate was added
  3. washthe mixture washed with aqueous sodium bicarbonate and brine
  4. extractionThe organic extract
  5. customwas dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d2b5333f24ab4629a901975d2ae34067
Source dataset
uspto-grants-2003_10
Patent number
US06639076B1

Reaction notes

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