Diisopropylcarbodiimide → N-(27-hydroxyheptacosanoyl)-phytospingosine

HRID 581631Notes

Reaction equation

HRID 581631 reaction equation
C(N=C=NC(C)C)(C)C.[OH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][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][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([OH:39])=O.ON1C2C=CC=CC=2N=N1.[OH:50][CH2:51][C@@H:52]([C@@H:54]([C@@H:56]([CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])[OH:57])[OH:55])[NH2:53]>O1CCCC1>[OH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][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][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([NH:53][C@H:52]([C@@H:54]([C@@H:56]([CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH3:71])[OH:57])[OH:55])[CH2:51][OH:50])=[O:39]

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 122121PhytosphingosineHCID 1432517727-Hydroxyheptacosanoic acid

Product 1

HCID 131721297N-(27-hydroxyheptacosanoyl)-phytospingosine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylcarbodiimide (1 ml, 6.4 mmoles) was added to a stirred suspension of 27-hydroxy-heptacosanoic acid (2.13 g, 5 mmoles), dry tetrahydrofuran (50 ml), dried 1-hydroxy-benzotriazole (1.6 g, 13.5 mmoles) and phytosphingosine (1.5 g, 4.7 mmoles) at 40° C. under nitrogen. After stirring overnight the mixture was cooled to room temperature and the precipitate was filtered off and washed with 20 ml of tetrahydrofuran.

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with 20 ml of tetrahydrofuran

Sources & evidence

ORD record
ord-f5976b8e510a4e9a8d6fac17ddff2ad9
Source dataset
uspto-grants-1999_07
Patent number
US05919960

Reaction notes

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