Potassium Hydroxide → HCID 18652514, compound

HRID 1588246Notes

Reaction equation

HRID 1588246 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])[CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)C.[OH-].[K+]>C(O)C>[C:17]([NH:16][C@H:15]([C:14]([N:6]([CH:7]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]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 18652515HCID 18652515, compound

Product 1

HCID 18652514HCID 18652514, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

N-CBZ-L-Valyl-N-(cycloheptyl)glycine ethyl ester (11.2 g, 0.0259 mol) was dissolved in ethanol (300 mL) and treated with 1N KOH (27 mL) in portions of 5.0 mL at 0°-5° C. After the mixture was allowed to stir at room temperature over night the ethanol was removed under vacuum, and the residue treated with water. The residue was 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 isolated the product as a white semisolid (6.5 g) melting at 48°-51° C.

Workup

  1. customwas removed under vacuum
  2. additionthe residue 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 MgSO4, filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-2969bbcf13824699a9a876e2b4ae1826
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

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