Sodium Hydroxide → 7-[Cyano(4-hydroxynonyl)amino]-2-methylheptanoic acid

HRID 1729917Notes

Reaction equation

HRID 1729917 reaction equation
C([O:4][CH:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])[C:10]#[N:11])(=O)C.[OH-].[Na+]>C(O)C.O>[OH:4][CH:5]([CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:6][CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([CH3:23])[C:18]([OH:20])=[O:19])[C:10]#[N:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86734144HCID 86734144, compound

Product 1

HCID 714447117-[Cyano(4-hydroxynonyl)amino]-2-methylheptanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 7-[N-(4-acetoxynonyl)cyanamido] -2-methylheptanoate (7.6 g., 0.02 mole) in ethanol (50 ml.) is added a solution of sodium hydroxide (1.6 g., 0.04 mole) in water (15 ml.) and the reaction is stirred at ambient temperature for 20 hours. Then most of the ethanol is removed in vacuo and the residue taken up in water (150 ml.). The solution is extracted once with ether then acidified with hydrochloric acid (dil.). The oil that separates is extracted into ether, the ether is washed with brine, dried over sodium sulfate, then removed under vacuum to give 7-[N-(4-hydroxynonyl)cyanamido]-2-methylheptanoic acid as a yellow oil.

Workup

  1. customThen most of the ethanol is removed in vacuo
  2. extractionThe solution is extracted once with ether
  3. extractionThe oil that separates is extracted into ether
  4. washthe ether is washed with brine
  5. dry with materialdried over sodium sulfate
  6. customremoved under vacuum

Sources & evidence

ORD record
ord-74acb03a106e417b970cefe90ee5e55b
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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