Sodium Hydroxide → 2-Cyanomethyl-3-octadecylcarbamoyloxypropanol

HRID 728502Notes

Reaction equation

HRID 728502 reaction equation
C([O:9][CH2:10][CH:11]([CH2:35][C:36]#[N:37])[CH2:12][O:13][C:14](=[O:34])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=O)C1C=CC=CC=1.[OH-].[Na+].C(CC(COCCCCCCCCCCCCCCCC)CO)#N>CO.O1CCCC1>[C:36]([CH2:35][CH:11]([CH2:12][O:13][C:14](=[O:34])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:10][OH:9])#[N:37]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 148349942-Cyanomethyl-3-hexadecyloxypropanolHCID 541175562-Cyanomethyl-3-octadecylcarbamoyloxypropyl benzoate

Product 1

HCID 148349952-Cyanomethyl-3-octadecylcarbamoyloxypropanolYield 81.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.49 g (2.96 mM) of 2-cyanomethyl-3-n-octadecylcarbamoyloxypropyl benzoate n5', 1.66 ml (3.32 mM) of 2N aqueous sodium hydroxide in 15 ml of methanol and 15 ml of tetrahydrofuran is allowed to react by the same procedure as described in (137) and 966 mg (76.8% yield) of the titled compound Vn2 is obtained.

Workup

  1. customto react by the same procedure

Sources & evidence

ORD record
ord-9c494ecd3ab04e5282f6ce1367fbd713
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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