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

HRID 2267909Notes

Reaction equation

HRID 2267909 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-912c649fffd144dab955a9b9c1f4812d
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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