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

HRID 346176
Notes
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Reaction equation

HRID 346176 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 241
Benzene
Solvent

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-21cfeb1b6a624e999c1d039f19a069ff
Source dataset
uspto-grants-1991_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05061710

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes