Sodium Hydroxide → 4-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carboxylic acid

HRID 1929200Notes

Reaction equation

HRID 1929200 reaction equation
CC[O:3][C:4]([C:6]1[N:7](C(OC(C)(C)C)=O)[C:8]2[C:13]([CH:14]=1)=[C:12]([O:15][CH2:16][C:17]1[N:18]=[C:19]([CH3:22])[S:20][CH:21]=1)[CH:11]=[CH:10][CH:9]=2)=[O:5].[OH-].[Na+]>C(O)C>[CH3:22][C:19]1[S:20][CH:21]=[C:17]([CH2:16][O:15][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[CH:14]=[C:6]([C:4]([OH:5])=[O:3])[NH:7]3)[N:18]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 668421144-(2-Methyl-thiazol-4-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

Product 1

HCID 668416854-(2-Methyl-thiazol-4-ylmethoxy)-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

4-(2-Methyl-thiazol-4-ylmethoxy)-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (169) (1.75 g, 4.2 mmol) is dissolved in 20 ml of ethanol. After addition of a 0.5M aqueous sodium hydroxide solution (33.6 ml, 16.8 mmol) the solution is heated to 60° C. and stirred at this temperature for 18 h. Then the reaction mixture is evaporated and the residue is dissolved in ethyl acetate. AT 0° C. conc HCl is added until a pH of 1 is reached. The organic phase is washed with water and brine. The organic layers are dried over sodium sulphate, filtrated. The product crystallized upon evaporation and could be filtrated off.

Workup

  1. customThen the reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. additionAT 0° C. conc HCl is added until a pH of 1
  4. washThe organic phase is washed with water and brine
  5. dry with materialThe organic layers are dried over sodium sulphate
  6. filtrationfiltrated
  7. customThe product crystallized upon evaporation
  8. filtrationcould be filtrated off

Sources & evidence

ORD record
ord-3927141ad5cc45ab83b9284a02fee496
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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