Methanol → HCID 11611261, compound

HRID 250885Notes

Reaction equation

HRID 250885 reaction equation
[CH2:1]([N:3]([C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28]([OH:30])=[O:29])=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1)[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:5])[CH3:2].CO>C(OCC)(=O)C.[Pd]>[CH2:1]([N:3]([C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1)[C:4]([NH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 887MethanolHCID 11531614HCID 11531614, compound

Product 1

HCID 11611261HCID 11611261, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 400 mg (0.98 mmol, 1 eq) of (E)-3-[3′-(1-ethyl-3-heptylureido)biphenyl-4-yl]acrylic acid (prepared in Example 27 g) in 10 mL of ethyl acetate in the presence of 0.2 ml of methanol is stirred for 4 hours at room temperature in the presence of 200 mg (50% by mass) of 10% palladium-on-charcoal under a hydrogen atmosphere. The reaction medium is filtered through Celite and then evaporated to dryness. After crystallization from ethyl ether/pentane, 265 mg of 3-[3′-(1-ethyl-3-heptylureido)biphenyl-4-yl]propanoic acid are obtained in the form of a white powder (m.p.=70° C.). Yield=66%

Workup

  1. filtrationThe reaction medium is filtered through Celite
  2. customevaporated to dryness
  3. customAfter crystallization from ethyl ether/pentane, 265 mg of 3-[3′-(1-ethyl-3-heptylureido)biphenyl-4-yl]propanoic acid

Sources & evidence

ORD record
ord-9a471dcdd0754368b25ccee3362ed635
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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