Sodium Hydroxide → N-Boc-8-amino-2E-octenoic acid

HRID 2247819Notes

Reaction equation

HRID 2247819 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[C:16]([O:18]C)=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+]>CO>[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15679327Methyl N-Boc-8-amino-2E-octenoate

Product 1

HCID 15679328N-Boc-8-amino-2E-octenoic acidYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 10.7 g (39.4 mmoles) of (8) in 30 mL methanol was chilled in an ice bath and 59 mL of 1N sodium hydroxide was added. The ice bath was removed and the mixture was stirred at room temperature for 20 h. After evaporation of most of the methanol, the solution was acidified to pH 3 with 1N potassium bisulfate. The mixture was extracted with ether, and washed with water and brine. After drying over sodium sulfate and removal of solvent in vacuo, the residue was crystallized from ether - hexane to provide 9.55 g of the title compound (9), mp 76°-78° C. Anal. Calcd. for C13H23NO4 : C, 60.68; H, 9.01; N, 5.44. Found: C, 60.50; H, 9:00; N, 5.40.

Workup

  1. customThe ice bath was removed
  2. customAfter evaporation of most of the methanol
  3. extractionThe mixture was extracted with ether
  4. washwashed with water and brine
  5. dry with materialAfter drying over sodium sulfate and removal of solvent in vacuo
  6. customthe residue was crystallized from ether - hexane

Sources & evidence

ORD record
ord-7f36b3f0a9bf444eb8f3afdf180d6387
Source dataset
uspto-grants-1991_08
Patent number
US05037808

Reaction notes

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