Sodium Hydroxide → HCID 86746146, compound

HRID 1885989Notes

Reaction equation

HRID 1885989 reaction equation
C[N:2]([C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[C@H:3]([C:7]([OH:9])=[O:8])[CH:4]([CH3:6])[CH3:5].[NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O-:24])=[O:23].[OH-].[Na+]>CO>[C:10]([NH:2][C@H:3]([C:7]([OH:9])=[O:8])[CH:4]([CH3:5])[CH3:6])(=[O:15])[C:11]([CH3:12])([CH3:13])[CH3:14].[NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86746147HCID 86746147, compound

Product 1

HCID 86746146HCID 86746146, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 500 ml of methanol was dissolved 44 g of methyl N-pivaloyl-L-valine-6-aminohexanoate followed by addition of 150 ml of 1N sodium hydroxide and the mixture was stirred at room temperature for 45 minutes. The ethanol was then evaporated off and 1N HCl and, then, ether were added to the residue. The mixture was shaken to extract the reaction product into the ether. The water layer was removed and the ether layer was dried over magnesium sulfate anhydride and concentrated to dryness under reduced pressure to give 35 g (0.112 mol) of the desired compound.

Workup

  1. customThe ethanol was then evaporated off
  2. addition1N HCl and, then, ether were added to the residue
  3. stirringThe mixture was shaken
  4. extractionto extract the reaction product into the ether
  5. customThe water layer was removed
  6. dry with materialthe ether layer was dried over magnesium sulfate anhydride
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-740aa2b00d6c4626bbee9897a54592f2
Source dataset
uspto-grants-1992_09
Patent number
US05149426

Reaction notes

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