Sodium Hydroxide → Benzyl D-valinate

HRID 1006086Notes

Reaction equation

HRID 1006086 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-2db9f1617a1a4cc8871bf9b4251b894d
Source dataset
uspto-grants-2004_09
Patent number
US06787559B2

Reaction notes

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