HCID 15712464, compound → HCID 15712465, compound

HRID 703513Notes

Reaction equation

HRID 703513 reaction equation
[C:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[CH:11]([CH:20]([CH3:31])[C:21]([O:23]CC2C=CC=CC=2)=[O:22])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd]>[C:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=2)[CH:11]([CH:20]([CH3:31])[C:21]([OH:23])=[O:22])[CH2:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 15712464HCID 15712464, compound

Product 1

HCID 15712465HCID 15712465, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Thirty grams of benzyl 2-(1-benzoyl-5-methoxy-3-indolinyl)propionate were hydrogenated over palladium-on-carbon in ethanol to remove the benzyl ester group. 2-(1-Benzoyl-5-methoxy-3-indolinyl)propionic acid thus formed crystallized on cooling in the hydrogenation bomb and separated with the catalyst on filtration. The desired product was dissolved away from the catalyst by washing with hot ethanol. Ethanol was removed from the combined filtrate and washings by evaporation. The resulting residue was dissolved in tetrahydrofuran (THF). The THF solution was filtered and the THF removed from the filtrate in vacuo. The resulting residue was crystallized from about 500 ml. of ethanol; yield=21.2 g. of 2-(1-benzoyl-5-methoxy-3-indolinyl)propionic acid melting at 169°-70° C.

Workup

  1. customto remove the benzyl ester group

Sources & evidence

ORD record
ord-5d21d8a968594d4dbf8d3327ab275daa
Source dataset
uspto-grants-1991_01
Patent number
US04983622

Reaction notes

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