Hydrochloric Acid → HCID 10095637, compound

HRID 1492597Notes

Reaction equation

HRID 1492597 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH:21]([C:28]([O:30]C)=[O:29])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:16]([CH2:32][CH2:33][CH3:34])[CH:15]=3)[C:9]([CH2:11][CH3:12])=[N:10][C:5]2=[C:4]([CH3:35])[CH:3]=1.[OH-].[Na+].Cl>CO>[C:28]([CH:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:8]2[C:6]3=[N:7][C:2]([CH3:1])=[CH:3][C:4]([CH3:35])=[C:5]3[N:10]=[C:9]2[CH2:11][CH3:12])=[CH:15][C:16]=1[CH2:32][CH2:33][CH3:34])([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19385711HCID 19385711, compound

Product 1

HCID 10095637HCID 10095637, compoundYield 509.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.042 g (0.09 mmol) of the product of Step B dissolved in 1.0 mL of methanol was added 0.1 mL of a 1.0N solution of sodium hydroxide and the reaction mixture was stirred for 3 hours at room temperature. The reaction mixture was then adjusted to pH 7 with 1.0N hydrochloric acid and then partitioned between ethyl acetate and water. The organic layer was separated, dried (MgSO4), filtered, evaporated and then purified on a silica gel flash chromatography column eluted with chloroform-methanol-conc. ammonium hydroxide (80:15:1). Evaporation of the purified fractions and drying in vacuo afforded 0.21 g (51%) of the title compound as a white amorphous solid.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified on a silica gel flash chromatography column
  7. washeluted with chloroform-methanol-conc
  8. customEvaporation of the purified fractions
  9. customdrying in vacuo

Sources & evidence

ORD record
ord-1c874b496244490db98060353ed76b80
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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