Sodium Hydroxide → Benzyl D-valinate

HRID 2297967Notes

Reaction equation

HRID 2297967 reaction equation
[OH-].[Na+].FC(F)(F)C(O)=O.[CH2:10]([O:17][C:18](=[O:24])[C@@H:19]([CH:21]([CH3:23])[CH3:22])[NH2:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH2:10]([O:17][C:18](=[O:24])[C@@H:19]([CH:21]([CH3:22])[CH3:23])[NH2:20])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69764497d-Valine benzyl ester trifluoroacetic acid salt

Product 1

HCID 7350007Benzyl D-valinateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 N Sodium hydroxide (80 mL) was added to a solution of D-valine benzyl ester trifluoroacetic acid salt (10 g, 31.1 mmol) in methylene chloride (80 mL) and the reaction mixture was stirred until all the starting material was converted to the free amine. The organic phase was collected and washed with brine, dried over magnesium sulfate, and concentrated to give D-valine benzyl ester (5.35 g) as a clear oil.

Workup

  1. customThe organic phase was collected
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-de066459fd214151bc2e2182022b30d0
Source dataset
uspto-grants-2002_12
Patent number
US06492394B1

Reaction notes

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