Water → HCID 53818678, compound

HRID 275293Notes

Reaction equation

HRID 275293 reaction equation
Cl.[NH2:2][C@H:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17].O.CCOC(C)=O>CN(C=O)C>[CH3:15][S:16]([NH:2][C@H:3]([C:11]([O:13][CH3:14])=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 75736Methyl L-phenylalaninate hydrochloride

Product 1

HCID 53818678HCID 53818678, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2.51 g (20.0 mmol) of methyl L-phenylalaninate hydrochloride and 6.7 mL (48 mmol) of TEA in 50 mL of DMF was added 1.86 mL (24 mmol) of methanesulfonyl chloride. After 16 hours, the reaction mixture was added to 200 mL of H2O and 200 mL of EtOAc. The resulting layers were separated, and the organic layer was washed with 3×200 mL of H2O and dried. The resulting residue was chromatographed to yield 2.54 g (49%) of N-(methylsulfonyl)-L-phenylalanine, methyl ester (13), which was a clear colorless glass.

Workup

  1. customThe resulting layers were separated
  2. washthe organic layer was washed with 3×200 mL of H2O
  3. customdried
  4. customThe resulting residue was chromatographed

Sources & evidence

ORD record
ord-341331ae35f8400f9c0a945bda689cf8
Source dataset
uspto-grants-1995_02
Patent number
US05393747

Reaction notes

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