Glyceric acid → HCID 20074079, compound

HRID 704412

Reaction equation

HRID 704412 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:32](O)(=[O:37])[CH:33]([CH2:35][OH:36])[OH:34].ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(OCC)(=O)C>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][NH:29][C:35](=[O:36])[CH:33]([CH2:32][OH:37])[OH:34])=[CH:30][CH:31]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 752Glyceric acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 151155341-[4-(Heptyloxy)phenyl]methanamine

Product 1

HCID 20074079HCID 20074079, compoundYield 28.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dicyclohexylcarbodiimide (160 mg) was added to a solution of 200 mg of p-heptyloxybenzylamine, 150 mg of glyceric acid (65% aqueous solution) and 110 mg of 1-hydroxybenzotriazole in 2 ml of N,N-dimethylformamide. The reaction mixture was stirred at room temperature for 16 hours, then diluted with ethyl acetate, washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by preparative silica gel thin layer chromatography to give 80 mg of N-(p-heptyloxybenzyl)glyceramide.

Workup

  1. washwashed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative silica gel thin layer chromatography

Sources & evidence

ORD record
ord-26f1cdaaf02c4cd1b785cc204e3972b6
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Linked notes

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