Lithium Hydroxide → cis-1-Benzoyl-4-hydroxy-L-proline

HRID 1165973Notes

Reaction equation

HRID 1165973 reaction equation
[C:1]([N:9]1[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+]>C1COCC1.O>[C:1]([N:9]1[CH2:16][C@@H:15]([OH:17])[CH2:14][C@H:10]1[C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 14750322(4R)-1-Benzoyl-4-hydroxy-L-proline

Product 1

HCID 14750323cis-1-Benzoyl-4-hydroxy-L-prolineYield 71%

Reagents, catalysts & solvents 1

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

Procedure

A solution of lactone from Example 1, part A(5) (10.05 gm, 46.31 mmole) in THF-H2O (100 ml -18 ml) was treated slowly with 1M lithium hydroxide (60 ml). The reaction was stirred at room temperature under argon for 2 hours, concentrated and acidified to pH 6 with HCl. The solution was washed several times with ethyl acetate, acidified to pH 1 with HCl, saturated with sodium chloride and extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to an oil which was crystallized from dichloromethane-hexane to afford 7.7 gm (71%) of the title compound.

Workup

  1. concentrationconcentrated
  2. washThe solution was washed several times with ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to an oil which
  8. customwas crystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-f39164458098405b85ef2ff1d36ae2b9
Source dataset
uspto-grants-1990_03
Patent number
US04912231

Reaction notes

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