Hydrochloric Acid → HCID 23121806, compound

HRID 133697Notes

Reaction equation

HRID 133697 reaction equation
C([O:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]#[N:20])[CH:8]=[C:7]([C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][N:25]=2)=[O:22])[CH:6]=1)(=O)C.C[O-].[Na+].Cl>C1COCC1.CO>[N+:30]([C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:21](=[O:22])[C:7]2[CH:6]=[C:5]([OH:4])[CH:10]=[C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]#[N:20])[CH:8]=2)=[N:25][CH:26]=1)([O-:32])=[O:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 23121809HCID 23121809, compound

Product 1

HCID 23121806HCID 23121806, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 3-{[(5-nitropyridin-2-yl)amino]carbonyl}-5-[(2-cyanobenzyl)oxy]phenyl acetate (5710 mg) in THF (35 ml) was treated with 25% NaOMe in methanol (6 ml). Stirred at ambient temperature for 30 minutes. Acidified with 2 m hydrochloric acid (25 ml), then extracted with ethyl acetate (100 ml). The extract was washed with water (50 ml), brine (50 ml), dried over MgSO4. Volatile material was removed by evaporation to give a solid. This was washed with hot methanol to give the title compound (4358 mg) as a solid, LCMS rt=2.38 min (90.5%). ES+391.45 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (100 ml)
  2. washThe extract was washed with water (50 ml), brine (50 ml)
  3. dry with materialdried over MgSO4
  4. customVolatile material was removed by evaporation
  5. customto give a solid
  6. washThis was washed with hot methanol

Sources & evidence

ORD record
ord-9385f2234ea34787b6194e0d0d7ae85b
Source dataset
uspto-grants-2008_06
Patent number
US07390908B2

Reaction notes

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