2,3,4-Triacetoxy-1-{2-[2-(2-azido-ethoxy)ethoxy]acetyl}5-hydroxypentyl acetate → 2,3,4-Triacetoxy-1-{2-[2-(2-aminoethoxy)ethoxy]acetyl}-5-hydroxypentyl acetate

HRID 1725283Notes

Reaction equation

HRID 1725283 reaction equation
[C:1]([O:4][CH:5]([C:23](=[O:34])[CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][N:31]=[N+]=[N-])[CH:6]([O:19][C:20](=[O:22])[CH3:21])[CH:7]([O:15][C:16](=[O:18])[CH3:17])[CH:8]([O:11][C:12](=[O:14])[CH3:13])[CH2:9][OH:10])(=[O:3])[CH3:2]>C(O)C.[Ni]>[C:1]([O:4][CH:5]([C:23](=[O:34])[CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][NH2:31])[CH:6]([O:19][C:20](=[O:22])[CH3:21])[CH:7]([O:15][C:16](=[O:18])[CH3:17])[CH:8]([O:11][C:12](=[O:14])[CH3:13])[CH2:9][OH:10])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 865859692,3,4-Triacetoxy-1-{2-[2-(2-azido-ethoxy)ethoxy]acetyl}5-hydroxypentyl acetate

Product 1

HCID 235935112,3,4-Triacetoxy-1-{2-[2-(2-aminoethoxy)ethoxy]acetyl}-5-hydroxypentyl acetate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

In a hydrogenation apparatus, a suspension of 1.12 g of 2,3,4-triacetoxy-1-{2-[2-(2-azido-ethoxy)ethoxy]acetyl}-5-hydroxypentyl acetate and 1.0 g of Raney-Nickel in 100 ml of ethanol is shaken under an atmosphere of hydrogen for 4 h. The reaction solution is filtered and concentrated. The residue contains 23:

Workup

  1. filtrationThe reaction solution is filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3fdfb55c50fe46958ab575616941ae84
Source dataset
uspto-grants-2009_02
Patent number
US07488829B2

Reaction notes

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