Potassium Hydroxide → HCID 18631782, compound

HRID 1588243Notes

Reaction equation

HRID 1588243 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][N:6]([C:14](=[O:30])[C@H:15]([CH:27]([CH3:29])[CH3:28])[NH:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C.[OH-].[K+]>C(O)C>[C:17]([NH:16][C@H:15]([C:14]([N:6]([CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:5][C:4]([OH:31])=[O:3])=[O:30])[CH:27]([CH3:28])[CH3:29])([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18652513HCID 18652513, compound

Product 1

HCID 18631782HCID 18631782, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-CBZ-L-Valyl-N-(benzyl)glycine ethyl ester (17.3 g, 0.0406mol) was dissolved in ethanol (200 mL) and treated with 1N KOH (45 mL) in portions of 8.0 mL at 0-5C. The mixture was allowed to stir at room temperature over night. The ethanol was removed under reduced pressure, and the residue was treated with water. Extracted three times with ethyl acetate and afterwards the aqueous layer was acidified with 2N HCl. The product was extracted into ethyl acetate and washed with saturated aqueous sodium chloride. After drying over MgSO4, filtration and evaporation under reduced pressure afforded the product as a white semisolid (14.1 g) melting at 41°-45° C.

Workup

  1. customThe ethanol was removed under reduced pressure
  2. additionthe residue was treated with water
  3. extractionExtracted 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 MgSO4, filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-bd9bcb76749443f98ede12a5b6363b87
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

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