Aluminum(III) Chloride → trans-1-Benzoyl-4-phenyl-l-proline

HRID 1165972

Reaction equation

HRID 1165972 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[C:5]([N:13]1[CH2:20][C@@H:19](OS(C2C=CC(C)=CC=2)(=O)=O)[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>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:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 53847232(cis)-1-benzoyl-4-tosyloxy-L-proline

Product 1

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

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

To a dry flask was added aluminum trichloride (58 mg, 0.435 mmole) and benzene (3 ml). While stirring under argon, (cis)-1-benzoyl-4-tosyloxy-L-proline (50 mg, 0.128 mmole) was added. After further stirring overnight, the reaction was cooled to 0° C. and quenched with 1N HCl. The resulting mixture was extracted with ethyl acetate and the organic extracts were washed with brine, dried, and concentrated in vacuo. The residue consisted of:

Workup

  1. stirringAfter further stirring overnight
  2. customquenched with 1N HCl
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. washthe organic extracts were washed with brine
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a18c09f3d7dd49a59ba6e1fe620710c6
Source dataset
uspto-grants-1990_03
Patent number
US04912231

Linked notes

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