HCID 58009507, compound → HCID 58009531, compound

HRID 1009484Notes

Reaction equation

HRID 1009484 reaction equation
C([O:8][C:9]1[CH:38]=[CH:37][C:12]([CH2:13][NH:14][C:15](=[O:36])[CH2:16][N:17]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[C:29]=2[CH3:35])[S:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.C1COCC1.[Pd]>[Cl:34][C:30]1[C:29]([CH3:35])=[C:28]([N:17]([S:18]([C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)(=[O:19])=[O:20])[CH2:16][C:15]([NH:14][CH2:13][C:12]2[CH:37]=[CH:38][C:9]([OH:8])=[CH:10][CH:11]=2)=[O:36])[CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 1

HCID 58009507HCID 58009507, compound

Product 1

HCID 58009531HCID 58009531, compoundYield 66.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

668 mg of N-[4-(benzyloxy)benzyl]-N2-(3-chloro-2-methylphenyl)-N2-[(4-methylphenyl)sulfonyl]glycinamide was dissolved in 5.00 mL of methanol and 2.00 mL of THF, and 70 mg of 10% Pd—C (Kawaken, AD type, water content 54%) was added thereto, followed by stirring at room temperature for 6.5 hours under a hydrogen atmosphere. The reaction liquid was filtered through Celite, the filtrate was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50 to 30:70) to obtain a product, which was recrystallized from ethanol/water to obtain 373 mg of N2-(3-chloro-2-methylphenyl)-N-(4-hydroxybenzyl)-N2-[(4-methylphenyl)sulfonyl] glycinamide.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered through Celite
  3. customthe filtrate was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50 to 30:70)
  5. customto obtain a product, which
  6. customwas recrystallized from ethanol/water

Sources & evidence

ORD record
ord-8cabd35f2cf045d385c3e8151ca57d59
Source dataset
uspto-grants-2011_07
Patent number
US07973078B2

Reaction notes

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