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

HRID 651839Notes

Reaction equation

HRID 651839 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-homoserine 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-ad2d578c277a4e6e8f22133281aeb09c
Source dataset
uspto-grants-2001_08
Patent number
US06281364B1

Reaction notes

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