Sodium Hydroxide → 5-Bromo-3-{[(5-tert-butoxy-5-oxopentyl)amino]sulfonyl}-1H-indole-2-carboxylic acid

HRID 1676994Notes

Reaction equation

HRID 1676994 reaction equation
C([O:3][C:4]([C:6]1[N:7](S(C2C=CC=CC=2)(=O)=O)[C:8]2[C:13]([C:14]=1[S:15]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:17])=[O:16])=[CH:12][C:11]([Br:30])=[CH:10][CH:9]=2)=[O:5])C.[OH-].[Na+]>C1COCC1.O>[Br:30][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[C:14]2[S:15]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:16])=[O:17]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 67372682Ethyl-5-bromo-3-{[(5-tert-butoxy-5-oxopentyl)amino]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Product 1

HCID 673706595-Bromo-3-{[(5-tert-butoxy-5-oxopentyl)amino]sulfonyl}-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl-5-bromo-3-{[(5-tert-butoxy-5-oxopentyl)amino]sulfonyl}-1-(phenylsulfonyl)-1H-indole-2-carboxylate (63 mg, 0.98 mmol) in 2 mL of 3:1 THF/water was added NaOH (2 pellets). After stirring at room temperature for 6 hours, another portion of NaOH was added. After 16 hours, the reaction was partitioned between 3N HCl and dichloromethane. The aqueous phase was extracted three times with dichloromethane, and the combined organic phases were dried (Na2SO4), filtered, and concentrated in vacuo to give the titled product as a white foam. ESI+ MS: 419 [M-CH2═CMe2]+.

Workup

  1. waitAfter 16 hours
  2. customthe reaction was partitioned between 3N HCl and dichloromethane
  3. extractionThe aqueous phase was extracted three times with dichloromethane
  4. dry with materialthe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d89e6fc37014490ab25fe07134bd3c8
Source dataset
uspto-grants-2011_08
Patent number
US08008295B2

Reaction notes

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