Sodium Hydroxide → 5-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-1H-indole-2-carboxylic acid

HRID 724515Notes

Reaction equation

HRID 724515 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15](=[O:27])[NH:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+]>CO>[C:23]([O:22][C:20]([NH:19][CH2:18][CH2:17][NH:16][C:15]([C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[CH:14]2)=[O:27])=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 587471275-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-1H-indole-2-carboxylic acid ethyl ester2×

Product 1

HCID 587470885-(2-tert-Butoxycarbonylamino-ethylcarbamoyl)-1H-indole-2-carboxylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 31 was dissolved in MeOH (20 ml) and 2 M aqueous NaOH (10 ml) was added. The reaction mixture was stirred at room temperature for 2 h until no compound 31 was detected by TLC. The reaction solution was evaporated to about 8 ml and adjusted to pH 3 with 2 M HCl. The precipitates formed were collected by filtration or centrifugation, washed with water and dried under high vacuum to give a white powder (0.158 g) in total yield of 91%. MS 346.23 (M−H+). 1H NMR (DMSO-d6) 11.95 (s, 1H), 8.36 (t, 1H), 8.18 (s, 1H), 7.72 (d, 1H), 7.41 (d, 1H), 7.15 (s, 1H), 6.91 (t, 1H), 3.29 (q, 2H), 3.10 (q, 2H), 1.37 (s, 9H).

Workup

  1. customThe reaction solution was evaporated to about 8 ml
  2. customThe precipitates formed
  3. filtrationwere collected by filtration or centrifugation
  4. washwashed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-cdea177579c64f28979ebed9661c65f7
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

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