Sodium Hydroxide → 5-(4-Carboxy-thiazol-2-yl)-indole-1-carboxylic acid tert-butyl ester

HRID 460204Notes

Reaction equation

HRID 460204 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[S:18][CH:19]=[C:20]([C:22]([O:24]CC)=[O:23])[N:21]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[S:18][CH:19]=[C:20]([C:22]([OH:24])=[O:23])[N:21]=3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 694116205-(4-Ethoxycarbonyl-thiazol-2-yl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 694111395-(4-Carboxy-thiazol-2-yl)-indole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(4-ethoxycarbonyl-thiazol-2-yl)-indole-1-carboxylic acid tert-butyl ester (3.34 g, 9.0 mmol) and 125 mL of THF was added 1N NaOH (aq) (30.0 mL, 30.0 mmol). The solution was stirred for 24 h then concentrated in vacuo. The crude solid was redissolved in H2O and acidified with 5% KHSO4. The solid was filtered and dried in vacuo at 60° C. to give a pinkish-white solid. MS m/z: 345 (M+1). Calc'd for C17H16N2O4S-344.39.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe crude solid was redissolved in H2O
  3. filtrationThe solid was filtered
  4. customdried in vacuo at 60° C.
  5. customto give a pinkish-white solid

Sources & evidence

ORD record
ord-2f5a70cc6c484a068ef7530656514d7c
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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