Potassium Hydroxide → HCID 18649006, compound

HRID 373765Notes

Reaction equation

HRID 373765 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][N:6]([C:16](=[O:32])[C@H:17]([CH:29]([CH3:31])[CH3:30])[NH:18][C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])[CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)C.[OH-].[K+]>C(O)C>[C:19]([NH:18][C@H:17]([C:16]([N:6]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8]1)[CH2:5][C:4]([OH:33])=[O:3])=[O:32])[CH:29]([CH3:30])[CH3:31])([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 18649007HCID 18649007, compound

Product 1

HCID 18649006HCID 18649006, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-CBZ-L-Valyl-N-(2-indanyl)glycine ethyl ester (13.8 g, 0.0305 mol) was dissolved in ethanol (200 mL) and treated with 1N KOH (30 mL) in 5 mL portions. After the mixture was allowed to sit at room temperature overnight, the ethanol was removed under vacuum, and the residue treated with water. The aqueous mixture was washed three times with ethyl acetate and the layers separated. The aqueous layer was acidified to pH 3 with 1N HCl. The product was extracted into ethyl acetate and washed with saturated aqueous NaCl-solution. After drying over MgSO4, filtration and evaporation under reduced pressure afforded the product as a white semi-solid (9.1 g).

Workup

  1. customthe ethanol was removed under vacuum
  2. additionthe residue treated with water
  3. washThe aqueous mixture was washed three times with ethyl acetate
  4. customthe layers separated
  5. extractionThe product was extracted into ethyl acetate
  6. washwashed with saturated aqueous NaCl-solution
  7. dry with materialAfter drying over MgSO4, filtration and evaporation under reduced pressure

Sources & evidence

ORD record
ord-6a34dbc0cf624556b1c62b6482b87060
Source dataset
uspto-grants-1992_11
Patent number
US05166154

Reaction notes

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