Hydrochloric Acid → HCID 66657596, compound

HRID 420985Notes

Reaction equation

HRID 420985 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][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:13]=2)[N:8]([C:27]2[CH:32]=[CH:31][C:30]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[CH:29][CH:28]=2)[C:7]=1[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[O:5])C.Cl.[OH-].[Na+]>CCO>[CH2:36]([N:33]([CH2:34][CH3:35])[C:30]1[CH:29]=[CH:28][C:27]([N:8]2[C:9]3[C:14](=[CH:13][C:12]([O:15][C:16]4[CH:17]=[CH:18][C:19]([O:22][C:23]([F:25])([F:24])[F:26])=[CH:20][CH:21]=4)=[CH:11][CH:10]=3)[C:6]([C:4]([OH:5])=[O:3])=[C:7]2[CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:32][CH:31]=1)[CH3:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66657737HCID 66657737, compound

Product 1

HCID 66657596HCID 66657596, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(4-diethylaminophenyl)-2-ethoxycarbonylmethyl-5-(4-trifluoromethoxyphenoxy)indole-3-carboxylic acid ethyl ester (63 mg, 0.12 mmol, see step (a) Example 75), HCl (aq, 1 M, 0.2 mL) and EtOH (1 mL) was heated at reflux for 2 h and cooled. The pH was adjusted to 4 by with NaOH (aq, 1 M) and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), concentrated and purified by chromatography to give the title compound. Yield 61 mg (89%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. extractionthe mixture was extracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified by chromatography

Sources & evidence

ORD record
ord-ce27645caeed4c2a9a2d53b3afbc483b
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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