Sodium Hydroxide → 5-(((tert-butoxy)carbonyl)amino)-1H-indole-2-carboxylic acid

HRID 1455897Notes

Reaction equation

HRID 1455897 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([O:20]CC)=[O:19])=[CH:12]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([OH:20])=[O:19])=[CH:12]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22105416Ethyl 5-[(tert-butoxycarbonyl)amino]-1H-indole-2-carboxylate

Product 1

HCID 158871475-(((tert-butoxy)carbonyl)amino)-1H-indole-2-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 30 (2.61 g, 8.6 mmol) in methanol (200 mL) was treated with 3N sodium hydroxide solution (50 mL) , and the reaction mixture was stirred for 18 h at room temperature. Solvent was removed. Water (100 mL) was added. The solution was neutralized with 20% hydrochloric acid and the precipitate was filtered to give compound 31 (2.03 g, 86%) as a yellow solid. m.p.192°-193° C. 1H NMR (DMSO-d6, ppm) 12.83 (brs, 1 H, COOH), 11.69 (s, 1 H, NH), 9.13 (s, 1 H, CONH), 7.79-7.04 (m, 4 H, Ar--H), 1.48 (s, 9 H, C(CH3)3). Anal. (C14H16N2O4 0.5H2 O), C, H, N.

Workup

  1. customSolvent was removed
  2. additionWater (100 mL) was added
  3. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-6f71194463a44a299927b89802cb6edf
Source dataset
uspto-grants-1998_12
Patent number
US05843937

Reaction notes

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