Benzyl 1-tert-butoxycarbonyl-2-ethoxycarbonylindole-4-carboxylate → 1-Tert-butoxycarbonyl-2-ethoxycarbonylindole-4-carboxylic acid

HRID 1533752Notes

Reaction equation

HRID 1533752 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([O:19]CC3C=CC=CC=3)=[O:18])[C:11]=2[CH:10]=[C:9]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)=O.CO>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([OH:19])=[O:18])[C:11]=2[CH:10]=[C:9]1[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 18355068Benzyl 1-tert-butoxycarbonyl-2-ethoxycarbonylindole-4-carboxylate

Product 1

HCID 183548601-Tert-butoxycarbonyl-2-ethoxycarbonylindole-4-carboxylic acidYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent2×

Procedure

To a mixture of 10% palladium on charcoal (130 mg) in 5.0% formic acid-methanol (5.0 ml) was added a solution of benzyl 1-tert-butoxycarbonyl-2-ethoxycarbonylindole-4-carboxylate (130 mg) in 5.0% formic acid-methanol (5.0 ml). The mixture was stirred under nitrogen atmosphere at ambient temperature for 30 minutes. The resulting mixture was filtered through a bed of celite and the filtrate was evaporated in vacuo to give 1-tert-butoxycarbonyl-2-ethoxycarbonylindole-4-carboxylic acid (87 mg) as a white crystal.

Workup

  1. filtrationThe resulting mixture was filtered through a bed of celite
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-2309c82a694e42e4a86bd70c98803cd6
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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