Hydrochloric Acid → trans-1-Benzoyl-4-phenyl-l-proline

HRID 1165965Notes

Reaction equation

HRID 1165965 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5]([N:13]1[CH2:20][C@@H:19](F)[CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>C1C=CC=CC=1>[C:5]([N:13]1[CH2:20][C@H:19]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:18][C@H:14]1[C:15]([OH:17])=[O:16])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 14584914(cis)-1-Benzoyl-4-fluoro-L-proline

Product 1

HCID 46864073trans-1-Benzoyl-4-phenyl-l-proline

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A suspension of aluminum trichloride (191 mg, 1.43 mmole) in benzene (5 ml) was stirred under argon and treated with Part B (cis)-N-benzoyl-4-fluoro-L-proline (100 mg, 0.42 mmole). The reaction was stirred at room temperature for 20 hours, cooled to 0° C. and hydrolyzed with 1N HCl. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried and concentrated. The residue consisted of

Workup

  1. stirringThe reaction was stirred at room temperature for 20 hours
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5d1c8a6155244098807a146718398f92
Source dataset
uspto-grants-1990_03
Patent number
US04912231

Reaction notes

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