HCID 19829260, compound → HCID 19829261, compound

HRID 1493862Notes

Reaction equation

HRID 1493862 reaction equation
C([O:8][CH:9]([CH2:30][O:31][C:32](=[O:37])[NH:33][CH2:34][CH2:35][Br:36])[CH2:10][O: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][CH3:29])C1C=CC=CC=1>[Pd].C(O)(=O)C>[Br:36][CH2:35][CH2:34][NH:33][C:32]([O:31][CH2:30][CH:9]([OH:8])[CH2:10][O: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][CH3:29])=[O:37]

Participants

4

Reactant 1

HCID 19829260HCID 19829260, compound

Product 1

HCID 19829261HCID 19829261, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A 40 ml portion of 90% aqueous acetic acid solution was added to 949 mg (1.623 mmole) of 2-benzyl-3-O-(2'-bromoethyl)carbamoyl-1-octadecylglycerol (as synthesized in Example 7) and 250 mg of 10% Pd/C, and hydrogenolysis was carried out at room temperature for 2 hours. After the catalyst was filtered out, the filtrate was concentrated under reduced pressure, and a mixture of n-hexane-ethyl acetate (2:1) was added to the residue. The precipitate was collected by filtration to give 785 mg (97.8 g.) of the alcohol derivative (colorless powder).

Workup

  1. filtrationAfter the catalyst was filtered out
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additiona mixture of n-hexane-ethyl acetate (2:1)
  4. additionwas added to the residue
  5. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-3a28f7602c4c48dab879c2bfcc789067
Source dataset
uspto-grants-1991_06
Patent number
US05025005

Reaction notes

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