Hydrochloric Acid → [6-Chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-acetic acid

HRID 505075Notes

Reaction equation

HRID 505075 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[C:7]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])=[CH:6]1.O[Li].O.Cl>C1COCC1.CO.O.CCOC(C)=O>[Cl:14][C:11]1[CH:12]=[C:13]2[C:8]([C:7]([C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])=[CH:6][N:5]2[CH2:4][C:3]([OH:21])=[O:2])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 66743651[6-Chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-acetic acid methyl ester

Product 1

HCID 66743777[6-Chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-acetic acidYield 99%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To as stirred solution of 2 g (6.3 mmol) of [6-chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-acetic acid methyl ester in 45 ml of THF/MeOH/H2O 1/1/1, at 40° C., were added 0.79 g (18.9 mmol, 3 eq.) of LiOH.H2O. After 1 hour, the reaction mixture was diluted in EtOAc, acidified with aq.HCl 1M. The organic phase were dried over Na2SO4, and concentrated under vacuo to afford 1.9 g (99%) of [6-chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-acetic acid as a white solid.

Workup

  1. dry with materialThe organic phase were dried over Na2SO4
  2. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-872791eb75134282aba1f74f6497b304
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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