Ammonium formate → HCID 91361322, compound

HRID 2307760Notes

Reaction equation

HRID 2307760 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C@H:11]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=2)=[CH:2]1.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:20][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][CH:17]=1)[O:13][CH2:12][C@@H:11]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:27])[CH3:28])[CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 91456250HCID 91456250, compound

Product 1

HCID 91361322HCID 91361322, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 20A (247 mg, 0.600 mmol), ammonium formate (400 mg, 6.34 mmol) and 10% Pd/C (25 mg) in methanol (10 mL) was heated to reflux for 30 minutes, cooled to room temperature, filtered through diatomaceous earth (Celite®), and concentrated. The concentrate was purified by flash column chromatography on silica gel with ethyl acetate/hexanes (1:1) to provide the desired product (200 mg, 87%). MS (DCI/NH3) m/e 382 (M+H)+.

Workup

  1. temperatureto reflux for 30 minutes
  2. filtrationfiltered through diatomaceous earth (Celite®)
  3. concentrationconcentrated
  4. customThe concentrate was purified by flash column chromatography on silica gel with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-62ed381a59a5427db6cd32213409b63f
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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