Acetic Acid → Methyl 3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate

HRID 250846Notes

Reaction equation

HRID 250846 reaction equation
[CH2:1]([NH:8][C:9](=[O:31])[N:10]([C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([O:28][CH3:29])=[O:27])=[CH:20][C:19]=2[OH:30])[CH:15]=[CH:16][CH:17]=1)[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(O)(=O)C>CO.C(OCC)(=O)C.[Pd]>[CH2:1]([NH:8][C:9](=[O:31])[N:10]([C:12]1[CH:13]=[C:14]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:20][C:19]=2[OH:30])[CH:15]=[CH:16][CH:17]=1)[CH3:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 67273468methyl(E)-3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]acrylate

Product 1

HCID 11582687Methyl 3-[3'-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoateYield 60%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.89 g (13.87 mmol, 1 eq) of methyl (E)-3-[3′-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]acrylate in 10 ml of methanol and 10 mL of ethyl acetate in the presence of 3 mL of acetic acid and 1.0 g (17% by mass) of 10% palladium-on-charcoal is stirred for 12 hours at room temperature under a hydrogen atmosphere. The palladium is filtered off through Celite and the solvents are evaporated off. The residue is chromatographed on silica gel (7/3 heptane/ethyl acetate) and crystallized from pentane. 3.0 g of methyl 3-[3′-(3-heptyl-1-methylureido)-2-hydroxybiphenyl-4-yl]propanoate are obtained in solid form. Yield=60%

Workup

  1. filtrationThe palladium is filtered off through Celite
  2. customthe solvents are evaporated off
  3. customThe residue is chromatographed on silica gel (7/3 heptane/ethyl acetate)
  4. customcrystallized from pentane

Sources & evidence

ORD record
ord-a602e9a22fc54a02a9ce661e23ba5455
Source dataset
uspto-grants-2011_01
Patent number
US07863332B2

Reaction notes

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