Methanesulfonyl chloride → (2R)-N-methanesulfonyl-(4-chlorophenyl)alanine methyl ester

HRID 1670016Notes

Reaction equation

HRID 1670016 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C@@H:4]([CH3:13])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C@@H:4]([CH3:13])[N:5]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[S:16]([CH3:15])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 69805663(2R)-4-chlorophenylalanine methylester

Product 1

HCID 967649(2R)-N-methanesulfonyl-(4-chlorophenyl)alanine methyl esterYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2R)-4-chlorophenylalanine methylester (213 mg, 1.00 mmol) in DCM (5 mL) was added dropwise TEA (280 μl, 2.00 mmol) and then methanesulfonylchloride (100 μl, 1.3 mmol) at 0° C. After 30 min, the reaction mixture was quenched with water and extracted with DCM and EtOAc. The organic solution was washed with 1N HCl, dried over MgSO4 and concentrated in vacuo, and the residue was purified by column chomatography (MeOH/CHCl3=1/25) to give the title compound (280 mg, 96.1%).

Workup

  1. customat 0° C
  2. customthe reaction mixture was quenched with water
  3. extractionextracted with DCM and EtOAc
  4. washThe organic solution was washed with 1N HCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customthe residue was purified by column chomatography (MeOH/CHCl3=1/25)

Sources & evidence

ORD record
ord-22fdeb6094e141c19676282c45696651
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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