HCID 86584546, compound → HCID 69654868, compound

HRID 1061215Notes

Reaction equation

HRID 1061215 reaction equation
[N:1]([CH2:4][C@@H:5]([C:7]1[CH:8]=[CH:9][C:10]([O:23]CC2C=CC=CC=2)=[C:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:12]=1)[OH:6])=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][CH2:4][C@@H:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:23])=[C:11]([NH:13][S:14]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)(=[O:16])=[O:15])[CH:12]=1)[OH:6]

Participants

4

Reactant 1

HCID 86584546HCID 86584546, compound

Product 1

HCID 69654868HCID 69654868, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of N-[5-((1R)-2-azido-1-hydroxy-ethyl)-2-benzyloxy-phenyl]-benzenesulfonamide (1.4 g, 3.3 mmol) (which was obtained in Example 31), HCO2NH4 (2.08 g, 3.3 mmol), and 10% Pd/C in absolute ethanol (15 mL) under nitrogen atmosphere was heated under reflux for 2.5 hours. The mixture was cooled to room temperature, filtered through celite pad, and filtrate concentrated and placed under high vacuum to give the titled compound as yellow solid (0.7 g, 69%); 1H NMR (300 MHz, DMSO-d6) δ 2.74 (d, J=15 Hz, 2H), 4.51 (d, J=6 Hz, 1H), 6.63 (d, J=9 Hz, 1H), 6.76 (d, J=9 Hz, 1H), 7.12 (s, 1H), 7.47 (m, 4H), 7.72 (d, J=6 Hz, 2H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. filtrationfiltered through celite pad, and filtrate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d2256a91de24423cacfaf2286c2a8c59
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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