HCID 53248104, compound → HCID 20561417, compound

HRID 882669Notes

Reaction equation

HRID 882669 reaction equation
[N:1]([CH2:4][CH:5]([S:10]([OH:13])(=[O:12])=[O:11])[CH2:6][C:7]([OH:9])=[O:8])=[N+]=[N-]>[Pd].CO>[NH2:1][CH2:4][CH:5]([S:10]([OH:13])(=[O:11])=[O:12])[CH2:6][C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 53248104HCID 53248104, compound

Product 1

HCID 20561417HCID 20561417, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 500 ml of hydrogenation bottle was added 4-azido-3-sulfobutanoic acid (3.00 g, 14.35 mmol), 150 ml of methanol and 0.32 g of Pd/C (10% Pd, 50% wet). After sucked out air, 30 psi of H2 was conducted, and the mixture was shaken overnight, filtered through celite, evaporated, and coevaporated with dry EtOH to afford about 2.50 g (95%) of 4-amino-3-sulfobutanoic acid. 1H NMR (CD3OD) 3.24 (m, 1H), 3.17 (m, 1H), 2.90 (dd, 1H, J=2.6, 16.5 Hz), 2.33 (dd, 1H, J=10.1, 16.5 Hz), ESI MS m/z−181.60 (M−H). The resulted compound was unstable and was used directly without further purification.

Workup

  1. filtrationfiltered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-330b3628d6254f7b93c405ba3bcb6a2e
Source dataset
uspto-grants-2012_08
Patent number
US08236319B2

Reaction notes

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