HCID 59219186, compound → HCID 59219086, compound

HRID 2247415Notes

Reaction equation

HRID 2247415 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])[CH:13]=[CH:14][C:15]=1Cl)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[C].[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:17]2[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=2)[C:20]([O:22][CH3:23])=[O:21])[CH:13]=[CH:14][CH:15]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 59219186HCID 59219186, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59219086HCID 59219086, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

Methyl 3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-chlorophenyl)benzoate (199 mg) was dissolved in 3 ml of methanol, 100 mg of 10% palladium-carbon was added thereto, and the mixture was stirred at room temperature for 3 days in a hydrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was evaporated. The residue was dissolved in ethyl acetate, then washed with a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and the solvent was evaporated, to give 182 mg of the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with a saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e1816aa4fb8f43188853fd5e30d444fd
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

Loading…