Benzyl 5-(4'-(1-(ethoxycarbonyl)cyclopropyl)biphenyl-4-yl)-3-methylisoxazole-4-carboxylate → 5-(4'-(1-(Ethoxycarbonyl)cyclopropyl)biphenyl-4-yl)-3-methylisoxazole-4-carboxylic acid

HRID 557624Notes

Reaction equation

HRID 557624 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[C:27]([O:29]CC4C=CC=CC=4)=[O:28])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[C:27]([OH:29])=[O:28])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 66660603Benzyl 5-(4'-(1-(ethoxycarbonyl)cyclopropyl)biphenyl-4-yl)-3-methylisoxazole-4-carboxylate

Product 1

HCID 666602775-(4'-(1-(Ethoxycarbonyl)cyclopropyl)biphenyl-4-yl)-3-methylisoxazole-4-carboxylic acidYield 85.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The benzyl ester from Step 8 (1 g, 2.1 mmol) in ethyl acetate (10 mL) was degassed with nitrogen for 10 minutes. 10% Palladium on activated carbon (0.2 g, 0.2 mmol) was added and the solution was sparged with hydrogen via balloon. The balloon of hydrogen was maintained on the head space and the solution stirred for 1.5 hours. The reaction was diluted with ethanol and actone (to solublize the product), filtered through celite and evaporated to yield 700 mg product.

Workup

  1. customthe solution was sparged with hydrogen via balloon
  2. temperatureThe balloon of hydrogen was maintained on the head space
  3. additionThe reaction was diluted with ethanol and actone (
  4. filtrationfiltered through celite
  5. customevaporated

Sources & evidence

ORD record
ord-5431fa575b4f4161a0b3e479e5942927
Source dataset
uspto-grants-2011_11
Patent number
US08058300B2

Reaction notes

Loading…