2,3,4-Tri-O-acetyl-1-O-[4-(4-benzyloxycarbonylaminobutyl)phenyl]glucopyranuronic Acid Methyl Ester → 2,3,4-Tri-O-acetyl-1-O-[4-(4-aminobutyl)phenyl]glucopyranuronic Acid Methyl Ester

HRID 25124Notes

Reaction equation

HRID 25124 reaction equation
[CH3:1][O:2][C:3](=[O:44])[C@H:4]1[O:31][CH:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(OCC3C=CC=CC=3)=O)=[CH:12][CH:11]=2)[C@H:7]([O:32][C:33](=[O:35])[CH3:34])[C@@H:6]([O:36][C:37](=[O:39])[CH3:38])[C@@H:5]1[O:40][C:41](=[O:43])[CH3:42]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:44])[C@H:4]1[O:31][CH:8]([O:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])=[CH:14][CH:15]=2)[C@H:7]([O:32][C:33](=[O:35])[CH3:34])[C@@H:6]([O:36][C:37](=[O:39])[CH3:38])[C@@H:5]1[O:40][C:41](=[O:43])[CH3:42]

Participants

4

Reactant 1

HCID 687902142,3,4-Tri-O-acetyl-1-O-[4-(4-benzyloxycarbonylaminobutyl)phenyl]glucopyranuronic Acid Methyl Ester

Product 1

HCID 673668532,3,4-Tri-O-acetyl-1-O-[4-(4-aminobutyl)phenyl]glucopyranuronic Acid Methyl EsterYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Glucuronide 38 (1.5 g, 2.4 mmol) was dissolved in dry methanol (100 mL) and Pd/C (0.62 g, 5%) was added. The reaction mixture was stirred under hydrogen (1 atm) for 2.5 h at room temperature. After this time, the solution was passed through a pad of silica gel and the solvent was evaporated under reduced pressure to give amine 39 (0.94 g, 84%). 1H NMR (300 MHz, CDCl3) δ 1.46 (m, 2H), 1.60 (m, 2H), 2.08 (m, 9H), 2.58 (m, 2H), 2.72 (m, 2H), 3.63 (s, 3H), 4.14 (m, 1H), 5.10 (m, 1H), 5.34 (m, 3H), 6.90 (d, 2H), 7.12 (d, 2H).

Workup

  1. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e3c5dd0922a44db0b35b044695155d6b
Source dataset
uspto-grants-2005_02
Patent number
US06858615B2

Reaction notes

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