Hydrochloric Acid → HCID 66658227, compound

HRID 420988Notes

Reaction equation

HRID 420988 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][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=3)[CH:13]=2)[N:8]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)[C:7]=1[CH2:33][C:34]([O:36]CC)=[O:35])=[O:5])C.[OH-].[Na+].Cl>CCO>[C:34]([CH2:33][C:7]1[N:8]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[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:17]=[CH:18][C:19]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][CH:21]=1)=[CH:11][CH:10]=2)([OH:36])=[O:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66657731HCID 66657731, compound

Product 1

HCID 66658227HCID 66658227, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-(3-chlorophenyl)-2-ethoxycarbonylmethyl-5-(4-isopropoxyphenoxy)indole-3-carboxylic acid ethyl ester (65 mg, 0.12 mmol, see step (a) above), NaOH (aq, 1 M, 15 mL), and EtOH (20 mL) was heated at 50° C. for 48 h and stirred at rt overnight and acidified to pH 4 with HCl (aq, 1 M) and extracted with CH2Cl2. The organic layer was washed with H2O and brine, dried (Na2SO4), concentrated and purified by chromatography. Yield 45 mg (78%), mp 188-190° C.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by chromatography

Sources & evidence

ORD record
ord-bfab42fe2b2d4d0b84c9e65e5fadea0a
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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