Lithium Hydroxide → (2R)-N-methanesulfonyl-(4-chlorophenyl)alanine

HRID 1670017Notes

Reaction equation

HRID 1670017 reaction equation
C[O:2][C:3](=[O:18])[C@@H:4]([CH3:17])[N:5]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[S:6]([CH3:9])(=[O:8])=[O:7].[Li+].[OH-]>O.CO>[CH3:9][S:6]([N:5]([C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1)[C@@H:4]([C:3]([OH:18])=[O:2])[CH3:17])(=[O:7])=[O:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 967649(2R)-N-methanesulfonyl-(4-chlorophenyl)alanine methyl ester

Product 1

HCID 967528(2R)-N-methanesulfonyl-(4-chlorophenyl)alanineYield 94.3%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (2R)-N-methanesulfonyl-(4-chlorophenyl)alanine methylester, prepared in Step A, in water/methanol (5 mL, 1/1) was added portionwise LiOH (70.0 mg, 2.00 mmol). After being stirred at rt for 3 h, the reaction mixture was concentrated, and the residue was diluted with 1N HCl solution. The organic material was extracted with EtOAc, the extracts were concentrated in vacuo to give the title compound (179 mg, 94.3%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionthe residue was diluted with 1N HCl solution
  3. extractionThe organic material was extracted with EtOAc
  4. concentrationthe extracts were concentrated in vacuo

Sources & evidence

ORD record
ord-17e24dfe560444e78f5a74562a9c6df4
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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