Water → L-Prolinanilide

HRID 2186475Notes

Reaction equation

HRID 2186475 reaction equation
C([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.O>C(Cl)Cl>[C:16]1([NH:15][C:13]([C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[O:14])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 10606626HCID 10606626, compound

Product 1

HCID 6552381L-ProlinanilideYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-(+)-N-Boc-2-phenylaminocarbonylpyrrolidine (1.1 g, 3.8 mmol) in 5 mL of CH2Cl2 at 0° C. was added 5 mL of TFA dropwise over 1 hour. The solution was warmed to room temperature and stirred for 1.5 hours. To the reaction mixture was added 100 mL of water and the aqueous layer was washed with EtOAc. The aqueous layer was then made basic with 30 mL of 10% NaOH and extracted therein with 20 mL EtOAc. The organic layer was then dried over Na2SO4, filtered and concentrated under reduced pressure to give a white solid (0.40 g, 56%). ES (+) MS m/e=191 (M+H).

Workup

  1. washthe aqueous layer was washed with EtOAc
  2. extractionextracted
  3. dry with materialThe organic layer was then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-768dd623eea847aaa1d8a5ac10ea0370
Source dataset
uspto-grants-2002_06
Patent number
US06403792B1

Reaction notes

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