Ammonium formate → HCID 69745281, compound

HRID 495720Notes

Reaction equation

HRID 495720 reaction equation
[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:20][CH:21]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:22]1[CH:23]=[N:24][C:25](Cl)=[CH:26][CH:27]=1)[CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)[CH2:20][CH:21]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86585802HCID 86585802, compound

Product 1

HCID 69745281HCID 69745281, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred slurry of [2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl]-[2-(4-nitro-phenoxy)-ethyl]-carbamic acid tert-butyl ester (530 mg) and 10% palladium-on-carbon (530 mg) in MeOH (20 mL) was added ammonium formate (1.2 g). After 1.5 h, the reaction mixture was filtered through Celite® washing with methanol and concentrated in vacuo. The residue was suspended in half-saturated aqueous sodium bicarbonate, washed with ethyl acetate (3×), the combined organic phases were dried (Na2SO4) and concentrated in vacuo. The resulting oil was chromatographed on a Biotage® F40S column (40% ethyl acetate/hexanes) to afford 290 mg of the title compound (I-3d) as a colorless oil.

Workup

  1. filtrationthe reaction mixture was filtered through Celite®
  2. washwashing with methanol
  3. concentrationconcentrated in vacuo
  4. washwashed with ethyl acetate (3×)
  5. dry with materialthe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting oil was chromatographed on a Biotage® F40S column (40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-816a38549f0642f7aa4405569bd1bd38
Source dataset
uspto-grants-2005_09
Patent number
US06939867B2

Reaction notes

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