Hydrochloric Acid → 7-[Carbamoyl(4-hydroxynonyl)amino]-2-methylheptanoic acid

HRID 1729918Notes

Reaction equation

HRID 1729918 reaction equation
[OH-:1].[Na+].[OH:3][CH:4]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:20])[C:17]([OH:19])=[O:18])[C:9]#[N:10].OO.Cl>O.C(O)C>[OH:3][CH:4]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:5][CH2:6][CH2:7][N:8]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH3:20])[C:17]([OH:19])=[O:18])[C:9]([NH2:10])=[O:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 714447117-[Cyano(4-hydroxynonyl)amino]-2-methylheptanoic acid

Product 1

HCID 537658347-[Carbamoyl(4-hydroxynonyl)amino]-2-methylheptanoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of sodium hydroxide (0.4 g., excess) in water (50 ml.) and ethanol (50 ml.) is added 7-[N-(4-hydroxynonyl)-cyanamido]-2-methylheptanoic acid (1.5 g., 0.005 mole). The clear solution that is obtained is treated with 30% hydrogen peroxide (1.25 ml., excess). After two hours the reaction is poured into water (125 ml.), acidified with 5% hydrochloric acid and extracted with ethyl acetate (3 × 75 ml.). The organic phase is washed with brine, then dried over sodium sulfate. Evaporation of the solvent yields 7-[1-(4-hydroxynonyl)ureido]-2-methyl-heptanoic acid as a viscous oil.

Workup

  1. customThe clear solution that is obtained
  2. extractionextracted with ethyl acetate (3 × 75 ml.)
  3. washThe organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-54d993bc314b469095cf939955a95166
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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