Lithium hydroxide, monohydrate → HCID 10969363, compound

HRID 1779965Notes

Reaction equation

HRID 1779965 reaction equation
C[O:2][C:3](=[O:25])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:24])[CH2:10][CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O.[OH-].[Li+]>COCCOC.O>[C:18]1([CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][C:9]([N:5]2[CH2:6][CH2:7][CH2:8][C@H:4]2[C:3]([OH:25])=[O:2])=[O:24])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 13932900HCID 13932900, compound

Product 1

HCID 10969363HCID 10969363, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

N-(3,3-diphenylpropionyl)-L-proline methylester (2.10 g, 6.23 mmol) was dissolved in DME (50 ml) and H2O (50 ml). Lithium hydroxide monohydrate (1.57 g, 37.39 mmol) was added and the mixture was stirred at ambient temperature for 2 hrs. The reaction mixture was concentrated to remove DME and the remaining aqueous layer was acidified with 1N HCl to pH 3. The acidic layer was washed with EtOAc (3×75 ml). Organic washes were combined, dried with Na2SO4, filtered and concentrated to give 1.92 g (94%) of N-(3,3-diphenylpropionyl)-L-proline.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove DME
  3. washThe acidic layer was washed with EtOAc (3×75 ml)
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f756452bda1543f3bf6ea9b720102691
Source dataset
uspto-grants-1997_05
Patent number
US05629324

Reaction notes

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