Hydrochloric Acid → HCID 58934292, compound

HRID 2243162Notes

Reaction equation

HRID 2243162 reaction equation
C([O:3][C:4](=[O:38])[C:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=3)[CH:14]=2)[N:9]([C:27]2[CH:32]=[CH:31][C:30]([O:33][C:34]([F:37])([F:36])[F:35])=[CH:29][CH:28]=2)[CH:8]=1)=[O:6])C.[Li+].[OH-].Cl>C1COCC1>[F:37][C:34]([F:35])([F:36])[O:33][C:30]1[CH:31]=[CH:32][C:27]([N:9]2[C:10]3[C:15](=[CH:14][C:13]([C:16]4[CH:17]=[CH:18][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:20][CH:21]=4)=[CH:12][CH:11]=3)[C:7]([C:5](=[O:6])[C:4]([OH:38])=[O:3])=[CH:8]2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86593497HCID 86593497, compound

Product 1

HCID 58934292HCID 58934292, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.142 g [1,5-bis-(4-trifluoromethoxy-phenyl)-1H-indol-3-yl]-oxo-acetic acid ethyl ester from Step 3 in 1 mL THF was added 2 ml 0.5M aqueous LiOH. The reaction was mixed using orbital shaking for 5 hr, at which time TLC indicated that the reaction was complete. The solution was acidified by the dropwise addition of 2N aqueous HCl and extracted with dichloromethane. The organic phase was dried by filtration through a ChemElute column (Varian Inc., Palo Alto, Calif.) and the solvent was evaporated to afford 82 mg [1,5-Bis-(4-trifluoromethoxy-phenyl)-1H-indol-3-yl]-oxo-acetic acid as a yellow solid: 1H NMR (CDCl3, 400 MHz) δ 9.13 (s, 1H), 8.64 (s, 1H), 7.70 (d, J=6.6 Hz, 2H), 7.57-7.68 (m, 3H), 7.46-7.56 (m, 3H), 7.33 (d, J=8 Hz, 2H), MS: m/z (ESI) 508.2 (M−H);

Workup

  1. additionThe reaction was mixed
  2. extractionextracted with dichloromethane
  3. customThe organic phase was dried by filtration through a ChemElute column (Varian Inc., Palo Alto, Calif.)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4ac41d08d5e04770b94341797a55570d
Source dataset
uspto-grants-2010_03
Patent number
US07674818B2

Reaction notes

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