Hydrochloric Acid → (2S)-4-(acetyloxy)-2-(2,2,2-trifluoroacetamido)butanoic acid

HRID 2298548Notes

Reaction equation

HRID 2298548 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[C:8]([O:11][CH2:12][CH2:13][C@@H:14]([C:16]([OH:18])=[O:17])[NH2:15])(=[O:10])[CH3:9].C(OC(=O)C[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])C.Cl>C(O)C.O>[F:26][C:25]([F:28])([F:27])[C:24]([NH:15][C@H:14]([C:16]([OH:18])=[O:17])[CH2:13][CH2:12][O:11][C:8](=[O:10])[CH3:9])=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 45038083O-Acetyl-L-homoserine hydrochloride

Product 1

HCID 53989376(2S)-4-(acetyloxy)-2-(2,2,2-trifluoroacetamido)butanoic acidYield 45.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7.6 g (55 mol) of potassium carbonate are added to a suspension of 9.9 g (50 mmol) of O-acetyl-L-homoserine hydrochloride and 7.8 g (55 mmol) of trifluoroacetylacetic acid ethyl ester in 200 ml of ethanol, and stirring is carried out for 14 hours. 10.8 g (110 mmol) of 37% hydrochloric acid and 200 ml of water are then added. The product obtained after removal of the ethanol by distillation is filtered off with suction, washed with water and dried. 5.8 g (45%) of N-trifluoroacetyl-O-acetyl-L-homo-serine are obtained.

Workup

  1. customThe product obtained
  2. customafter removal of the ethanol
  3. distillationby distillation
  4. filtrationis filtered off with suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-709a559984004df2a1237fba515d1dd0
Source dataset
uspto-grants-2002_12
Patent number
US06492541B2

Reaction notes

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