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

HRID 2292165
Notes
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Reaction equation

HRID 2292165 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[C:24](=O)[CH3:25])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:25]1[CH:24]=[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 ethylacetate (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-6b6afe6765ca442f85b5af219dbd55d3
Source dataset
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04801609

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes