HCID 22601167, compound → HCID 22601170, compound

HRID 1250287Notes

Reaction equation

HRID 1250287 reaction equation
[N:1]([CH2:4][C:5]([CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])([CH2:7][O:8][CH2:9][CH2:10][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][CH3:30])[CH3:6])=[N+]=[N-].[H][H]>O1CCCC1.[OH-].[OH-].[Pd+2]>[NH2:1][CH2:4][C:5]([CH2:7][O:8][CH2:9][CH2:10][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][CH3:30])([CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH3:6]

Participants

5

Reactant 2

HCID 22601167HCID 22601167, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22601170HCID 22601170, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-Azido-2,2-bis(docosyloxymethyl)propane (12.8 g; 16.8 mmol) and palladium hydroxide on carbon (6.0 g) in tetrahydrofuran (100 ml) was stirred under the hydrogen atmosphere at 50° C. for 3 h. The reaction solution was filtered through celite, and the filtrate was evaporated to dryness in vacuo. The residue was purified by silica gel column chromatography (60 g of gel, chloroform/methanol, 10:1) to obtain the title compound (8 g, 65%) as white powder.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customthe filtrate was evaporated to dryness in vacuo
  3. customThe residue was purified by silica gel column chromatography (60 g of gel, chloroform/methanol, 10:1)

Sources & evidence

ORD record
ord-7f383e39122c4a73b0585357e4dda6ba
Source dataset
uspto-grants-2002_01
Patent number
US06337390B1

Reaction notes

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