HCID 15712464, compound → HCID 15712465, compound

HRID 1494625Notes

Reaction equation

HRID 1494625 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-9198d3ea54cd4d959fb40da18b314cf8
Source dataset
uspto-grants-1991_06
Patent number
US05026869

Reaction notes

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