Sodium Hydroxide → HCID 86745471, compound

HRID 1534334Notes

Reaction equation

HRID 1534334 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:20])[C@H:6]([CH2:16][CH:17]([CH3:19])[CH3:18])[NH:7][C:8](=[O:15])[C@H:9]([CH:12]([CH3:14])[CH3:13])[N:10]=[O:11]>CO>[O:11]=[N:10][C@H:9]([C:8]([NH:7][C@H:6]([C:5]([OH:20])=[O:4])[CH2:16][CH:17]([CH3:18])[CH3:19])=[O:15])[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86745470HCID 86745470, compound

Product 1

HCID 86745471HCID 86745471, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

113.5 ml of a 2N sodium hydroxide solution were added to a solution of 22.1 g of the ketovalylleucine methyl ester obtained in Example 10 in 200 ml of methanol, and the mixture was stirred for 1 hour. The methanol solvent was subsequently removed under reduced pressure, and the resulting aqueous solution was buffered with saturated ammonium chloride solution. After the mixture had been adjusted to pH 2 with 6N hydrochloric acid, it was extracted with dichloromethane. The collected organic phases were dried over sodium sulfate, and after filtration, the solvent was removed under reduced pressure. 15.0 g of the title compound were obtained in the form of an oil. The compound proved to have properties identical to those of the product obtained in Example 8.

Workup

  1. customThe methanol solvent was subsequently removed under reduced pressure
  2. extractionwas extracted with dichloromethane
  3. dry with materialThe collected organic phases were dried over sodium sulfate
  4. filtrationafter filtration
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f1fad7eeafee40ca8ca29291dfd88da2
Source dataset
uspto-grants-1992_02
Patent number
US05089492

Reaction notes

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