Citric Acid → HCID 86628819, compound

HRID 420933Notes

Reaction equation

HRID 420933 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]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=3)[CH:13]=2)[N:8]([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:7]=1[CH2:37][C:38]([O:40]CC)=[O:39])=[O:5])C.[OH-].[Na+].CCO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C1COCC1>[C:38]([CH2:37][C:7]1[N:8]([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]2[C:14]([C:6]=1[C:4]([OH:5])=[O:3])=[CH:13][C:12]([O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:24])([F:25])[F:23])=[CH:18][N:17]=1)=[CH:11][CH:10]=2)([OH:40])=[O:39]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86628818HCID 86628818, compound

Product 1

HCID 86628819HCID 86628819, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(4-trifluoromethoxyphenyl)-2-ethoxycarbonylmethyl-5-(5-trifluoromethyl-2-pyridinyloxy)indole-3-carboxylic acid ethyl ester (80 mg, 0.13 mmol, see step (a) above), NaOH (aq, 1 M, 1.1 mL), EtOH (0.5 mL) and THF (0.5 mL) was stirred at 100° C. for 9 h, cooled, diluted with H2O and acidified to pH 5 with citric acid (aq, 1 M). The precipitate was collected, washed with H2O and Et2O to give the title compound, 30 mg (42%), mp 203° C.

Workup

  1. temperaturecooled
  2. customThe precipitate was collected
  3. washwashed with H2O and Et2O

Sources & evidence

ORD record
ord-2b9ad317ff804c3d90b19fe9b53111d4
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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