Methanol → n-Benzyl-n-(3-chloro-4-fluorophenyl)alanine lithium salt

HRID 1822176Notes

Reaction equation

HRID 1822176 reaction equation
[CH2:1]([N:8]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=1)[C@H:9]([C:11]([O:13]C)=[O:12])[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.CO.O[Li:31].O>O>[Li+:31].[CH2:1]([N:8]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=1)[C@H:9]([C:11]([O-:13])=[O:12])[CH3:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68982233methyl N-benzyl-N-(3-chloro-4-fluorophenyl)alaninate

Product 1

HCID 68981703n-Benzyl-n-(3-chloro-4-fluorophenyl)alanine lithium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl N-benzyl-N-(3-chloro-4-fluorophenyl)alaninate (2-1, 0.870 g, 2.704 mmol) in a 3:1:1 mixture of THF:MeOH:H2O (100 mL) was treated with LiOH hydrate (0.119 g, 2.974 mmol) then stirred 24 h. Upon completion, the reaction mixture was concentrated under vacuum to yield N-benzyl-N-(3-chloro-4-fluorophenyl)alanine lithium salt (2-2). MS 308.2 found, 308.7 (M+H+) required.

Workup

  1. concentrationUpon completion, the reaction mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-9de40df84bc341899073b0184ef57dbf
Source dataset
uspto-grants-2009_10
Patent number
US07608739B2

Reaction notes

Loading…