Methyl iodide → HCID 66771920, compound

HRID 1697697Notes

Reaction equation

HRID 1697697 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([SH:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].CI.[C:20]([O-])(O)=O.[Na+]>CO>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10][CH3:20])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 72208118HCID 72208118, compound

Product 1

HCID 66771920HCID 66771920, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (2S,4R)-4-mercapto-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (9.5 g, 35.4 mmol) in MeOH (300 ml) were added methyl iodide (24 ml, 363.5 mmol) and NaHCO3 (3.4 g, 39.98 mmol). The reaction mixture was stirred for 12 h at 25° C. After complete consumption of the starting material, the solvent was removed under reduced pressure to get the crude material that was purified by column chromatography over silica gel (25-40% EtOAc/hexane) to obtain the title compound as white solid (6.9 g, 24.4 mmol; 69%). MS (ESI): m/z=276.4 [M+H]+.

Workup

  1. customAfter complete consumption of the starting material
  2. customthe solvent was removed under reduced pressure
  3. customto get the crude material that
  4. customwas purified by column chromatography over silica gel (25-40% EtOAc/hexane)

Sources & evidence

ORD record
ord-54f5c76419c94f4fa852c9f6145a75ed
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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