Hydrochloric Acid → 4-Benzoyl-2(S)-trifluoroacetamidobutyric acid

HRID 1651710Notes

Reaction equation

HRID 1651710 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][C@@H:6]1[C:12](=[O:13])[O:11][C:9](=[O:10])[CH2:8][CH2:7]1)=[O:4].[Al+3].[Cl-].[Cl-].[Cl-].Cl.C(O[CH2:25][CH3:26])(=O)C>C1C=CC=CC=1>[C:9]([CH2:8][CH2:7][C@H:6]([NH:5][C:3](=[O:4])[C:2]([F:15])([F:14])[F:1])[C:12]([OH:11])=[O:13])(=[O:10])[C:26]1[CH:25]=[CH:8][CH:7]=[CH:6][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 2779007N-[(3S)-2,6-dioxooxan-3-yl]-2,2,2-trifluoroacetamideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 143908104-Benzoyl-2(S)-trifluoroacetamidobutyric acid

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Heat at reflux for 3 hours a mixture of N-trifluoroacetyl-L-glutamic anhydride (18.0 g, 80 mmol) and AlCl3 (23.5 g, 177 mmol) in dry benzene (400 ml). Allow to cool, treat with ice (400 ml), conc. HCl (100 ml), and ethyl acetate (EtOAc) (400 ml). Dry the organic layer and concentrate to obtain the title compound as a brown crystalline solid (25 g).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 3 hours
  3. temperatureAllow to cool
  4. customDry the organic layer
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-4a9c754dda7d49ea8109f50b9dee45b0
Source dataset
uspto-grants-1990_05
Patent number
US04929641

Reaction notes

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