Trifluoroacetic acid → HCID 68283891, compound

HRID 1527265Notes

Reaction equation

HRID 1527265 reaction equation
C([O:5][C:6](=[O:22])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=2)[C:10]([C:19](=[O:21])[CH3:20])=[CH:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:19]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:8]([CH2:7][C:6]([OH:22])=[O:5])[CH:9]=1)(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68283810HCID 68283810, compound

Product 1

HCID 68283891HCID 68283891, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3-acetyl-5-methoxy-indol-1-yl)-acetic acid tert-butyl ester (520 mg, 1.71 mmol) in CH2Cl2 (15 mL) was added TFA (1.32 mL, 17.1 mmol). The reaction mixture was stirred at RT overnight. Volatiles were evaporated, then the crude material was taken up in 5 mL of 1M aqueous NaOH solution and washed with CH2Cl2 which was discarded. The water phase was acidified to pH=1 by adding a 6M aqueous HCl solution, and then was extracted twice with AcOEt. The combined organic phases were dried (Phase separator) and evaporated to give the title compound. MS (LC/MS): 248.1 [M+H]+, 246.1 [M−H]−; tR (HPLC conditions c): 3.47 min.

Workup

  1. customVolatiles were evaporated
  2. washwashed with CH2Cl2 which
  3. additionby adding a 6M aqueous HCl solution
  4. extractionwas extracted twice with AcOEt
  5. customThe combined organic phases were dried (Phase separator)
  6. customevaporated

Sources & evidence

ORD record
ord-6117850d199b48c09aef837d2098bcb3
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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