Benzyl 23-(2-methoxyethyl)-2,5,8,11,14,17,20-heptaoxa-23-azapentacosan-25-yl(methyl)carbamate → N1-(2,5,8,11,14,17,20-Heptaoxadocosan-22-yl)-N-(2-methoxyethyl)-N2-methylethane-1,2-diamine

HRID 625511Notes

Reaction equation

HRID 625511 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:28][CH2:29][N:30](C)[C:31](=O)OCC1C=CC=CC=1)[CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27]>[Pd].CO>[CH3:27][O:26][CH2:25][CH2:24][O:23][CH2:22][CH2:21][O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][N:5]([CH2:4][CH2:3][O:2][CH3:1])[CH2:28][CH2:29][NH:30][CH3:31]

Participants

4

Reactant 1

HCID 66586933Benzyl 23-(2-methoxyethyl)-2,5,8,11,14,17,20-heptaoxa-23-azapentacosan-25-yl(methyl)carbamate

Product 1

HCID 86709221N1-(2,5,8,11,14,17,20-Heptaoxadocosan-22-yl)-N-(2-methoxyethyl)-N2-methylethane-1,2-diamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl 23-(2-methoxyethyl)-2,5,8,11,14,17,20-heptaoxa-23-azapentacosan-25-yl(methyl)carbamate 335a (2.58 g, 4.38 mmol) and palladium on carbon (10%, wet, 0.6 g) in methanol (30 mL) were stirred under a hydrogen atmosphere (balloon) for 2 hours. The mixture was filtered through celite and evaporated to give product as an oil (1.9 g, 99%); MS (ES, m/z): 455 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-238cc61fea17478d9747e3dc521cf5dd
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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