Methanol → n-(3-Chloro-4-fluorophenyl)-n-(3-methoxybenzyl)alanine lithium salt

HRID 1822180Notes

Reaction equation

HRID 1822180 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[C@H:10]([C:12]([O:14]C)=[O:13])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8].C1COCC1.CO.O[Li:33].O>O>[Li+:33].[Cl:1][C:2]1[CH:3]=[C:4]([N:9]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[C@H:10]([C:12]([O-:14])=[O:13])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 68982423methyl N-(3-chloro-4-fluorophenyl)-N-(3-methoxybenzyl)alaninate

Product 1

HCID 68983355n-(3-Chloro-4-fluorophenyl)-n-(3-methoxybenzyl)alanine lithium salt

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl N-(3-chloro-4-fluorophenyl)-N-(3-methoxybenzyl)alaninate (6-1, 0.510 g, 1.450 mmol) in a 3:1:1 mixture of THF:MeOH:H2O (100 mL) was treated with LiOH hydrate (0.067 g, 1.595 mmol) then stirred 24 h. Upon completion, the reaction mixture was concentrated under vacuum to yield N-(3-chloro-4-fluorophenyl)-N-(3-methoxybenzyl)alanine lithium salt (6-2). MS 338.2 found 338.8 (M+H+) required.

Workup

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

Sources & evidence

ORD record
ord-7e327a6b67e9485b8abb9aec42900f13
Source dataset
uspto-grants-2009_10
Patent number
US07608739B2

Reaction notes

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