Methyl iodide → S-methyl-D-penicillamine methyl ester

HRID 1602984Notes

Reaction equation

HRID 1602984 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([C:7]([SH:10])([CH3:9])[CH3:8])[NH2:6].[CH2:12]1CCN2C(=NCCC2)CC1.CI>CN(C=O)C>[CH3:2][O:3][C:4](=[O:11])[C@@H:5]([C:7]([S:10][CH3:12])([CH3:9])[CH3:8])[NH2:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12278508Methyl 3-mercapto-D-valinate hydrochloride

Product 1

HCID 18395020S-methyl-D-penicillamine methyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 0° C. solution of D-penicillamine methyl ester hydrochloride (0.250 g., 1.25 mmoles) in DMF (4 mL) was added DBU (0.382 ml., 2.56 mmoles), followed by methyl iodide (0.081 ml., 1.31 mmoles). After 1 hour, the solution was partitioned between brine and ethyl acetate, and the organic layer was dried over sodium sulfate and concentrated. The residue was purified on silica, eluting with 6% methanol in dichloromethane to give S-methyl-D-penicillamine methyl ester as a colorless oil in 81% yield: 1H--NMR (CDCl3) δ 1.25 (s, 3H) 1.35 (s, 3H), 2.02 (s, 3H), 3.44 (s,1H), 3.72 (s, 3H); FAB HRMS:expected (M+H)=178.0902, found (M+H)=178.0905.

Workup

  1. customthe solution was partitioned between brine and ethyl acetate
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified on silica
  5. washeluting with 6% methanol in dichloromethane

Sources & evidence

ORD record
ord-012d0c8d7fdf42e6af195a0edcb91cea
Source dataset
uspto-grants-1999_11
Patent number
US05985900

Reaction notes

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