Magnesium orthosilicate → 3-(Acetylamino)-N-(4-oxo-12(Z)-heneicosenyl)propan amide

HRID 1681682Notes

Reaction equation

HRID 1681682 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH:13]([OH:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:8])(=[O:3])[CH3:2].C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.[Cr](Cl)([O-])(=O)=O.[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>ClCCl>[C:1]([NH:4][CH2:5][CH2:6][C:7]([NH:9][CH2:10][CH2:11][CH2:12][C:13](=[O:31])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 66225Magnesium orthosilicateHCID 867464293-(acetylamino)-N-(4-hydroxy-12(Z)-heneicosenyl)propanamideHCID 178479088HCID 178479088, compound

Product 1

HCID 867464283-(Acetylamino)-N-(4-oxo-12(Z)-heneicosenyl)propan amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 160 mg portion of 3-(acetylamino)-N-(4-hydroxy-12(Z)-heneicosenyl)propanamide was dissolved in 5 ml of dichloromethane and treated with 157 mg of pyridium chlorochromate for 2 hours. The solution was passed through a short pad of hydrous magnesium silicate and washed repeatedly with fresh dichloromethane. The filtrate and washes were combined and evaporated, giving 92 mg of the desired product as an off-white solid, mp 123°-125° C.

Workup

  1. washwashed repeatedly with fresh dichloromethane
  2. customevaporated

Sources & evidence

ORD record
ord-33ad43920a414380bde36a066042e10f
Source dataset
uspto-grants-1992_12
Patent number
US05173510

Reaction notes

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