Hydrochloric Acid → HCID 66657513, compound

HRID 420930Notes

Reaction equation

HRID 420930 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][Cl:25])=[CH:20][N:19]=3)[CH:15]=2)[N:10]([C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=2)[C:9]=1[CH2:37][C:38]([O:40]CC)=[O:39])=[O:7])[CH3:4].Cl>O.CCO>[CH2:3]([O:5][C:6]([C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][Cl:25])=[CH:20][N:19]=3)[CH:15]=2)[N:10]([C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=2)[C:9]=1[CH2:37][C:38]([OH:40])=[O:39])=[O:7])[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66657744HCID 66657744, compound

Product 1

HCID 66657513HCID 66657513, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

NaOH (17 mg, 0.43 mmol) in water (5 mL) was slowly added to 5-(5-chloromethylpyridin-2-yloxy)-2-ethoxycarbonylmethyl-1-(4-trifluoromethoxyphenyl)indole-3-carboxylic acid ethyl ester (50 mg, 0.086 mmol, see step (a) above) in EtOH (15 mL). The mixture was stirred at rt for 48 h, neutralized by addition of HCl (aq), concentrated and purified by preparative TLC. Yield 35 mg (74%), mp 168-170° C.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative TLC

Sources & evidence

ORD record
ord-e1392bdcc94b4b63b1e59fe2b1aeb8dc
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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