Acetic Acid → Methyl 7-[acetyl(4-hydroxynonyl)amino]heptanoate

HRID 1288357Notes

Reaction equation

HRID 1288357 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][CH:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:6][CH2:7][CH2:8][N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:10](=[O:12])[CH3:11].C(O)(=O)C>CCOCC>[OH:4][CH:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:6][CH2:7][CH2:8][N:9]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:3])=[O:20])[C:10](=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9550DiazomethaneHCID 215039297-[Acetyl(4-hydroxynonyl)amino]heptanoic acid

Product 1

HCID 21503968Methyl 7-[acetyl(4-hydroxynonyl)amino]heptanoate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of diazomethane (approx. 2.5 g., 0.06 mole) in ether (100 ml.) is mixed with a solution of 7-[N-(4-hydroxynonyl)acetamido]heptanoic acid (9.8 g., 0.03 mole) (Example 1, Step C) in ether (50 ml.). The resulting solution is allowed to stand 4 hours at room temperature. Acetic acid is then added to destroy the excess diazomethane and the solution is washed with dilute sodium bicarbonate solution and water and dried over sodium sulfate. Evaporation of volatile materials at reduced pressure yields methyl 7-[N-(4-hydroxynonyl)acetamido]-heptanoate as a viscous oil.

Workup

  1. customto destroy the excess diazomethane
  2. washthe solution is washed with dilute sodium bicarbonate solution and water
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of volatile materials at reduced pressure

Sources & evidence

ORD record
ord-c447b90e60f24bd4bbd58883649da5f2
Source dataset
uspto-grants-1976_10
Patent number
US03987091

Reaction notes

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