Potassium Hydroxide → HCID 18652516, compound

HRID 1588234Notes

Reaction equation

HRID 1588234 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][N:6]([C:12](=[O:28])[C@H:13]([CH:25]([CH3:27])[CH3:26])[NH:14][C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)C.[OH-].[K+]>C(O)C>[C:15]([NH:14][C@H:13]([C:12]([N:6]([CH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH2:5][C:4]([OH:29])=[O:3])=[O:28])[CH:25]([CH3:26])[CH3:27])([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18652517HCID 18652517, compound

Product 1

HCID 18652516HCID 18652516, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N-CBZ-L-Valyl-N-(cyclopentyl)glycine ethyl ester (4.8 g, 0.0119 mol) was dissolved in ethanol (60 mL) and treated with 1N KOH (12.5 mL) in portions of 3 mL. After the mixture was allowed to stir at room temperature over night the ethanol was removed under vacuum, and the residue was treated with water. The residue was extracted three times with ethyl acetate and afterwards the aqueous layer was acidified with dilute HCl. The product was extracted into ethyl acetate and then washed with saturated aqueous sodium chloride. After drying over MgSO<, filtration and evaporation under reduced pressure afforded the product as a white semisolid (2.6 g).

Workup

  1. customwas removed under vacuum
  2. additionthe residue was treated with water
  3. extractionThe residue was extracted three times with ethyl acetate
  4. extractionThe product was extracted into ethyl acetate
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialAfter drying over MgSO<, filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-1621257698124402bec5cebf6d4f106e
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

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