Lithium Hydroxide → (cis)-1-Benzoyl-4-fluoro-L-proline

HRID 1165964Notes

Reaction equation

HRID 1165964 reaction equation
C[O:2][C:3](=[O:18])[C@@H:4]1[CH2:8][C@H:7]([F:9])[CH2:6][N:5]1[C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Li+]>O1CCCC1.O.O>[C:10]([N:5]1[CH2:6][C@@H:7]([F:9])[CH2:8][C@H:4]1[C:3]([OH:18])=[O:2])(=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 54485156(cis)-1-Benzoyl-4-fluoro-L-proline methyl ester

Product 1

HCID 14584914(cis)-1-Benzoyl-4-fluoro-L-proline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of Part A (cis)-1-benzoyl-4-fluoro-L-proline methyl ester (3.7 g, 14.74 mmole) in tetrahydrofuran-water (37 ml-7 ml) was added 31 ml of a 1N solution of lithium hydroxide in water. The reaction was stirred at room temperature for 2 hours. The tetrahydrofuran was evaporated, the pH of the residual aqueous solution was adjusted to 8 and extracted with ethyl acetate. The organic extracts were discarded. The aqueous phase was acidified to pH 2 with concentrated HCl and extracted with dichloromethane. The organic extracts were washed with brine and dried (sodium sulfate). The organic solution was filtered and concentrated to 2.9 g of solid.

Workup

  1. customThe tetrahydrofuran was evaporated
  2. extractionextracted with ethyl acetate
  3. extractionextracted with dichloromethane
  4. washThe organic extracts were washed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationThe organic solution was filtered
  7. concentrationconcentrated to 2.9 g of solid

Sources & evidence

ORD record
ord-4bbf6bae93c64e1bb5ed6879c9685194
Source dataset
uspto-grants-1990_03
Patent number
US04912231

Reaction notes

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