Sodium Hydroxide → HCID 57559129, compound

HRID 736070Notes

Reaction equation

HRID 736070 reaction equation
C[O:2][C:3]([C:5]1[C:11]2[NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH:6]=1)=[O:4].[OH-].[Na+]>CO.O>[CH2:9]1[C:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:12][C:11]=2[C:5]([C:3]([OH:4])=[O:2])=[CH:6][NH:7][CH2:8]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 666401921,6-dihydro-2H-azepino[4,5-b]indole-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester

Product 1

HCID 57559129HCID 57559129, compoundYield 49.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1,6-dihydro-2H-azepino[4,5-b]indole-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester (0.293 g, 0.62 mmol) in MeOH (4 mL) was added 4 N NaOH (2 mL) and the mixture was heated for 5 hours under nitrogen. After cooling, the reaction mixture was diluted with water and extracted with EtOAc. The aqueous layer was acidified with AcOH. Precipitate was collected by filtration and washed with water and ether and dried under high vacuum to give the title compound (70 mg); 1H-NMR (DMSO-d6): δ 11.40 (1H, s), 10.73 (1H, br s), 7.83 (1H, m), 7.73 (2H, d), 7.38 (1H, m), 7.25 (1H, m), 6.88 (2H, m), 3.45 (2H, t), 3.87 (3H, s), 3.2.98 (2H, t), MS (ES): 229 (MH+).

Workup

  1. temperaturethe mixture was heated for 5 hours under nitrogen
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. filtrationPrecipitate was collected by filtration
  5. washwashed with water and ether
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-d91021e9f63a4409ba16c6d311cf8dd4
Source dataset
uspto-grants-2009_09
Patent number
US07595311B2

Reaction notes

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