Hydrochloric Acid → 2-Acetylamino-5-amino-2-difluoromethylpentanoic acid

HRID 638405Notes

Reaction equation

HRID 638405 reaction equation
[NH2:1][C:2]([CH:17]([F:19])[F:18])([CH2:6][CH2:7][CH2:8][NH:9]C(OC(C)(C)C)=O)[C:3]([OH:5])=[O:4].[C:20](Cl)(=[O:22])[CH3:21].Cl>[OH-].[Na+]>[C:20]([NH:1][C:2]([CH:17]([F:18])[F:19])([CH2:6][CH2:7][CH2:8][NH2:9])[C:3]([OH:5])=[O:4])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 222347252-Amino-5-tert-butoxycarbonylamino-2-difluoromethylpentanoic acid

Product 1

HCID 199663382-Acetylamino-5-amino-2-difluoromethylpentanoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 2.9 g of 2-amino-5-tert-butoxycarbonylamino-2-difluoromethylpentanoic acid in 10.5 ml of 1M sodium hydroxide is added at 0° C. simultaneously 0.19 g of acetylchloride and 5 ml of 2M aqueous sodium hydroxide. The reaction mixture is stirred for 3 hours at room temperature. The alkaline aqueous solution is then adjusted to a pH of 2 with hydrochloric acid and extracted with ethylacetate. After usual work-up the solvent is evaporated and the residue taken up in trifluoroacetic acid. After concentration and purification by ion exchange chromatography on a resin 5-amino-2-acetylamino-2-difluoromethylpentanoic acid is obtained.

Workup

  1. extractionextracted with ethylacetate
  2. customAfter usual work-up the solvent is evaporated
  3. concentrationAfter concentration and purification by ion exchange chromatography on a resin 5-amino-2-acetylamino-2-difluoromethylpentanoic acid
  4. customis obtained

Sources & evidence

ORD record
ord-e83ed82e8ebb4183a53861c49a59f95d
Source dataset
uspto-grants-1985_12
Patent number
US04560795

Reaction notes

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