Stearoyl chloride → HCID 57223674, compound

HRID 482672Notes

Reaction equation

HRID 482672 reaction equation
[C:1](Cl)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:21]([N:39]([C@@H:53]1[O:61][C@H:60]([CH2:62][OH:63])[C@@H:58]([OH:59])[C@H:56]([OH:57])[C@H:54]1[OH:55])[C:40](=[O:52])[CH2:41][C:42](=[O:51])[CH2:43][CH2:44][C:45](=[O:50])[CH2:46][CH2:47][CH2:48][CH3:49])[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][CH2:37][CH3:38].C(N(CC)CC)C.C1(C)C=CC=CC=1.C(O)(C)C>O1CCCC1>[CH2:21]([N:39]([C@@H:53]1[O:61][C@H:60]([CH:62]([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH3:1])[OH:63])[C@@H:58]([OH:59])[C@H:56]([OH:57])[C@H:54]1[OH:55])[C:40](=[O:52])[CH2:41][C:42](=[O:51])[CH2:43][CH2:44][C:45](=[O:50])[CH2:46][CH2:47][CH2:48][CH3:49])[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][CH2:37][CH3:38]

Participants

6

Reactant 4

HCID 8212Stearoyl chlorideHCID 8471TriethylamineHCID 18601735HCID 18601735, compoundHCID 21881414Toluene isopropyl alcohol

Product 1

HCID 57223674HCID 57223674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

1.2 g (0.004 mol) of octadecanoyl chloride and 2.0 g (0.0034 mol) of N-octadecyl-N-3,6-dioxodecanoyl-β-D-glucopyranosylamine in 50 ml of tetrahydrofuran are initially taken, and 0.4 g of triethylamine (0.004 mol) is added at 0° C. The mixture is stirred for 1 day at 20° C., the solid is filtered off with suction and the solvent is removed in a water-pump vacuum. The residue is chromatographed on a column containing 250 g of silica gel, using as mobile phase 10:1 toluene/isopropanol, and 1.9 g (65% of theory) of N-octadecyl-N-3,6-dioxodecoyl-(6-stearyl-β-D-glucopyranosyl)-amine are obtained, having an Rf value of 0.296 (6:1 toluene/isopropanol).

Workup

  1. filtrationthe solid is filtered off with suction
  2. customthe solvent is removed in a water-pump vacuum
  3. customThe residue is chromatographed on a column
  4. additioncontaining 250 g of silica gel
  5. customare obtained

Sources & evidence

ORD record
ord-f4f4056478cb463eb5459611a675ae7e
Source dataset
uspto-grants-1986_03
Patent number
US04574122

Reaction notes

Loading…