Hydrochloric Acid → HCID 67280154, compound

HRID 1693329Notes

Reaction equation

HRID 1693329 reaction equation
[C:1]([O:5][C:6]([N:8](C(OC(C)(C)C)=O)[C:9]1[C:10]2[C:11]3[C:12](=[N:24][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:26]=2)[CH:13]=[C:14]([C:19]([O:21]CC)=[O:20])[C:15]=3[CH2:16][S:17][N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]2[C:11]3[C:12](=[N:24][N:25]([CH2:27][C:28]4[C:33]([CH3:34])=[C:32]([O:35][CH3:36])[C:31]([CH3:37])=[CH:30][N:29]=4)[N:26]=2)[CH:13]=[C:14]([C:19]([OH:21])=[O:20])[C:15]=3[CH2:16][S:17][N:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67280049HCID 67280049, compound

Product 1

HCID 67280154HCID 67280154, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-[bis(tert-butoxycarbonyl)amino]-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulene-8-carboxylate (0.92 g) was dissolved in methanol (10 ml) under cooling in an ice bath. A 1 N sodium hydroxide solution (10 ml) was added, and the mixture was stirred for 16 hours while gradually returning to room temperature. The reaction solution was neutralized with a 0.5 N hydrochloric acid solution, and then the solvent was concentrated. The resulting residue was diluted with chloroform and washed with a 10% citric acid solution, and the organic layer was dried over sodium sulfate. The solvent was evaporated, and the resulting residue was recrystallized from hexane and ethyl acetate to obtain the title compound as a solid (0.68 g, 91%).

Workup

  1. temperatureunder cooling in an ice bath
  2. customwhile gradually returning to room temperature
  3. concentrationthe solvent was concentrated
  4. additionThe resulting residue was diluted with chloroform
  5. washwashed with a 10% citric acid solution
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. customThe solvent was evaporated
  8. customthe resulting residue was recrystallized from hexane and ethyl acetate

Sources & evidence

ORD record
ord-10a2abdadfbd435996043bb5f8f8f9d4
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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