Sodium Hydroxide → HCID 66657747, compound

HRID 420969Notes

Reaction equation

HRID 420969 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[C:21]([C:22](=[O:24])N)=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:13]=2)[N:8]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH:32]([CH3:34])[CH3:33])=[CH:27][CH:26]=2)[C:7]=1[CH2:35][C:36]([O:38]CC)=[O:37])=[O:5])C.[OH-:41].[Na+]>CCO>[C:4]([CH2:6][C:7]1[N:8]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH:32]([CH3:33])[CH3:34])=[CH:29][CH:30]=2)[C:9]2[C:14]([C:35]=1[C:36]([OH:38])=[O:37])=[CH:13][C:12]([O:15][C:16]1[C:21]([C:22]([OH:24])=[O:41])=[CH:20][CH:19]=[CH:18][N:17]=1)=[CH:11][CH:10]=2)([OH:3])=[O:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66657538HCID 66657538, compound

Product 1

HCID 66657747HCID 66657747, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-(3-carbamoylpyridin-2-yloxy)-2-ethoxycarbonylmethyl-1-(4-isopropoxyphenyl)indole-3-carboxylic acid ethyl ester (63 mg, 0.12 mmol, see step (a) Example 65), NaOH (aq, 2M, 0.35 mL) and EtOH (2 mL) was stirred at 90° C. for 8 h, concentrated, diluted with MeOH and filtered through Celite®. EtOAc was added to the filtrate which was cooled for 4 h at 5° C. The solid was collected and dissolved in H2O. The mixture was acidified to pH 4 with HCl (aq, 2 M). The solid was filtered off and dried for 4 h at 60° C. to give the title compound. Yield 34 mg (60%), mp 212-214° C. after recrystallisation from EtOAc/MeOH.

Workup

  1. concentrationconcentrated
  2. additiondiluted with MeOH
  3. filtrationfiltered through Celite®
  4. additionEtOAc was added to the filtrate which
  5. temperaturewas cooled for 4 h at 5° C
  6. customThe solid was collected
  7. dissolutiondissolved in H2O
  8. filtrationThe solid was filtered off
  9. customdried for 4 h at 60° C.

Sources & evidence

ORD record
ord-f5e175d2a59e4ee1a1de815e6cdc6f77
Source dataset
uspto-grants-2012_01
Patent number
US08097623B2

Reaction notes

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