Ammonium formate → HCID 69954045, compound

HRID 2300234Notes

Reaction equation

HRID 2300234 reaction equation
[CH3:1][O:2][C:3](=[O:50])[CH2:4][N:5]([C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:22][CH:21]([N:23](CC3C=CC=CC=3)[CH2:24][CH:25]([OH:42])[CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([O:34]CC4C=CC=CC=4)=[CH:30][CH:29]=3)[CH2:20]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1)[CH2:6][CH2:7][CH2:8][CH3:9].C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:50])[CH2:4][N:5]([CH2:6][CH2:7][CH2:8][CH3:9])[C:10]1[CH:11]=[CH:12][C:13]([S:16]([N:19]2[CH2:22][CH:21]([NH:23][CH2:24][CH:25]([OH:42])[CH2:26][O:27][C:28]3[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=3)[CH2:20]2)(=[O:18])=[O:17])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69951756HCID 69951756, compound

Product 1

HCID 69954045HCID 69954045, compoundYield 115%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of {[4-(3-{Benzyl-[3-(4-benzyloxy-phenoxy)-2-hydroxy-propyl]-amino}-azetidine-1-sulfonyl)-phenyl]-butyl-amino}-acetic acid methyl ester (35 mg, 0.05 mmol) in methanol (2 ml) was added ammonium formate (49 mg, 0.75 mmol), and 8 mg of 10% Pd/C. The mixture was stirred at reflux for 18 h. After cooling to room temperature, it was filtered through Celite. The solvent was evaporated and the residue triturated with ether-hexanes to give 30 mg of an off-white foam; MS (ES) m/z 522.0 (MH+); HRMS (FAB) Calcd. for C25H36N3O7S (MH+): 522.2274, Found: 522.2293.

Workup

  1. temperatureat reflux for 18 h
  2. filtrationit was filtered through Celite
  3. customThe solvent was evaporated
  4. customthe residue triturated with ether-hexanes

Sources & evidence

ORD record
ord-02a2f58fe1d841daad5857a82ca14a2e
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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