Methyl 4-(N-(benzyloxycarbonyl)-4-methylbenzamido)-2-p-tolylthiophene-3-carboxylate → Methyl 4-(4-methylbenzamido)-2-p-tolylthiophene-3-carboxylate

HRID 1918218Notes

Reaction equation

HRID 1918218 reaction equation
C(OC([N:11]([C:21]1[C:22]([C:33]([O:35][CH3:36])=[O:34])=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)[S:24][CH:25]=1)[C:12](=[O:20])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=O)C1C=CC=CC=1>C(O)C.C(OCC)(=O)C.ClCCl.[Pd]>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]([NH:11][C:21]2[C:22]([C:33]([O:35][CH3:36])=[O:34])=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[S:24][CH:25]=2)=[O:20])=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 67052242Methyl 4-(N-(benzyloxycarbonyl)-4-methylbenzamido)-2-p-tolylthiophene-3-carboxylate

Product 1

HCID 67052278Methyl 4-(4-methylbenzamido)-2-p-tolylthiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22027680Ethanol ethyl acetate methylene chlorideSolvent

Procedure

10% Pd/C is added to compound 179 in ethanol:ethyl acetate:dichloromethane (2:1:1). The mixture is degassed and placed under H2 (1 atm) and stirred for 30 min The mixture is filtered through a 0.45 μm syringe filter and concentrated under reduced pressure to provide 180.

Workup

  1. customThe mixture is degassed
  2. filtrationis filtered through a 0.45 μm syringe
  3. filtrationfilter
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-209a53ce2d234ebba18a7b29ee4b42ac
Source dataset
uspto-grants-2013_12
Patent number
US08618307B2

Reaction notes

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