methyl(E)-3-[2-benzyloxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate → HCID 67273049, compound

HRID 250910Notes

Reaction equation

HRID 250910 reaction equation
C([O:8][C:9]1[CH:14]=[C:13](/[CH:15]=[CH:16]/[C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:11][C:10]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:36])[C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:29])[CH:22]=1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:12]=[CH:11][C:10]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]([CH3:36])[C:28]([NH:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[O:29])[CH:22]=1

Participants

5

Reactant 1

HCID 67273110methyl(E)-3-[2-benzyloxy-3'-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate

Product 1

HCID 67273049HCID 67273049, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a manner similar to that of Example (18e), by reaction of 400 mg (26% by mass) of 10% palladium-on-charcoal, 1.54 g (3.16 mmol, 1 eq) of methyl (E)-3-[2-benzyloxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]acrylate in 20 ml of methanol and 5 mL of ethyl acetate, and after crystallization from pentane, 1.1 g of methyl 3-[2-hydroxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate are obtained in solid form. Yield=87%

Workup

  1. customafter crystallization from pentane, 1.1 g of methyl 3-[2-hydroxy-3′-(1-methyl-3-pentylureido)biphenyl-4-yl]propanoate
  2. customare obtained in solid form

Sources & evidence

ORD record
ord-88e971a0e07d49029e28893975d7f08c
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

Loading…