Hydrochloric Acid → HCID 19385603, compound

HRID 1492594Notes

Reaction equation

HRID 1492594 reaction equation
[C:1]([CH:5]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:18]3=[N:19][C:20]([CH3:24])=[CH:21][C:22]([CH3:23])=[C:17]3[N:16]=[C:15]2[CH2:25][CH3:26])=[CH:9][C:8]=1[CH2:27][CH:28]=[CH2:29])([O:3]C)=[O:2].[OH-].[Na+].Cl>CO>[C:1]([CH:5]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][N:14]2[C:18]3=[N:19][C:20]([CH3:24])=[CH:21][C:22]([CH3:23])=[C:17]3[N:16]=[C:15]2[CH2:25][CH3:26])=[CH:9][C:8]=1[CH2:27][CH:28]=[CH2:29])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19385708HCID 19385708, compound

Product 1

HCID 19385603HCID 19385603, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.141 g (0.30 mmol) of the product of Step H dissolved in 2.0 mL of methanol was added 0.25 mL of a 1.0N solution of sodium hydroxide and the reaction was stirred at room temperature for 2 hours. 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 0.092 g (69%) 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-971c501108984aa7960e46a5279178e8
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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