Lithium Hydroxide → N-[1-(2,4-difluorophenyl)-2-(dimethylamino)-2-oxoethyl]-L-leucine

HRID 383966Notes

Reaction equation

HRID 383966 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:15][C@H:16]([C:21]([O:23]C)=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])[C:10]([N:12]([CH3:14])[CH3:13])=[O:11].[OH-].[Li+]>CO.O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:15][C@H:16]([C:21]([OH:23])=[O:22])[CH2:17][CH:18]([CH3:20])[CH3:19])[C:10]([N:12]([CH3:13])[CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68842657methyl N-[1-(2,4-difluorophenyl)-2-(dimethylamino)-2-oxoethyl]-L-leucinate

Product 1

HCID 68842051N-[1-(2,4-difluorophenyl)-2-(dimethylamino)-2-oxoethyl]-L-leucineYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl N-[1-(2,4-difluorophenyl)-2-(dimethylamino)-2-oxoethyl]-L-leucinate (100 mg) in methanol (3 ml) was added a solution of lithium hydroxide (15.4 mg) in water (1 ml). After stirring vigorously for 4 hours the solvent was removed in vacuo. The residue was diluted with water (10 ml) then neutralised with 2N hydrochloric acid. This solution was applied to an Oasis™ cartridge (6 g) and eluted with water (×2) and methanol (×2). The required fractions were combined and evaporated to afford N-[1-(2,4-difluorophenyl)-2-(dimethylamino)-2-oxoethyl]-L-leucine (95 mg).

Workup

  1. customwas removed in vacuo
  2. additionThe residue was diluted with water (10 ml)
  3. washeluted with water (×2) and methanol (×2)
  4. customevaporated

Sources & evidence

ORD record
ord-dab3d583b53d4339b11a9e5be16ef3e6
Source dataset
uspto-grants-2013_02
Patent number
US08367673B2

Reaction notes

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