HCID 19829260, compound → HCID 19829261, compound

HRID 649048Notes

Reaction equation

HRID 649048 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-4bb6c715af9346f291885072ef1f87a1
Source dataset
uspto-grants-1988_04
Patent number
US04737518

Reaction notes

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