Methyl iodide → methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinate

HRID 2185442Notes

Reaction equation

HRID 2185442 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.[C:9]([O:13][C:14]([NH:16][C@H:17]([C:28]([OH:30])=[O:29])[CH2:18][CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>CN(C=O)C>[CH3:1][O:29][C:28](=[O:30])[C@H:17]([CH2:18][CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH:16][C:14]([O:13][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:15]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15058464O-Benzyl-N-(tert-butoxycarbonyl)-L-homoserine

Product 1

HCID 54564501methyl O-benzyl-N-(tert-butoxycarbonyl)homoserinateYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.07 g), methyl iodide (1.25 mL) were added to a solution of N-tert-butoxycarbonyl-O-benzyl-L-homoserine (3.10 g) in DMF (15 mL). After stirring at room temperature for 5 hr, the solvent was removed in vacuo. Ethyl acetate and water were added to the residue. The separated organic layer was washed with brine, dried over sodium sulfate, and evaporated in vacuo to give the title compound (3.13 g) as a pale yellow oil: 1H NMR (400 MHz, CDCl3) δ 1.44 (m, 9H), 1.95-2.15 (m, 2H), 3.55 (m, 2H), 3.68 (s, 3H), 4.44 (m, 1H), 4.45 (d, J=11.6 Hz, 1H), 4.49 (d, J=11.7 Hz, 1H), 5.47 (m, 1H), and 7.27-7.37 (m, 5H).

Workup

  1. customthe solvent was removed in vacuo
  2. additionEthyl acetate and water were added to the residue
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-cf5b3d458fc5422599079aaa4a438a2c
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…