Ammonium formate → HCID 118236077, compound

HRID 1481300Notes

Reaction equation

HRID 1481300 reaction equation
C([O:8][CH:9]1[C:10](=[O:41])[NH:11][C:12]2[C:17]([C:18]3[CH:19]=[CH:20][N:21]=[C:22]([CH:35]=3)[C@@H:23]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:24][CH:25]=[CH:26]1)=[CH:16][CH:15]=[C:14]([NH:36][C:37]([O:39][CH3:40])=[O:38])[CH:13]=2)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[OH:8][CH:9]1[C:10](=[O:41])[NH:11][C:12]2[CH:13]=[C:14]([NH:36][C:37]([O:39][CH3:40])=[O:38])[CH:15]=[CH:16][C:17]=2[C:18]2[CH:35]=[C:22]([C@@H:23]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:24][CH:25]=[CH:26]1)[N:21]=[CH:20][CH:19]=2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 118236096HCID 118236096, compound

Product 1

HCID 118236077HCID 118236077, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 123A (770 mg, 1.378 mmol) in MeOH (125.00 mL) under Ar was added palladium hydroxide on carbon (77 mg, 0.551 mmol) and ammonium formate (3477 mg, 55.1 mmol). The mixture was refluxed at 65° C. overnight. The reaction mixture was filtered through Celite, rinsed with MeOH, and concentrated. The residue was purified by silica gel chromatography to yield 123B (360 mg, 0.765 mmol, 55.5% yield). MS (ESI) m/z: 471.2 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washrinsed with MeOH
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3e09e80b7112422086d10ab71c521728
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

Loading…