Hydrochloric Acid → HCID 86712923, compound

HRID 1424075Notes

Reaction equation

HRID 1424075 reaction equation
[Si]([O:8][CH2:9][C@:10]1([CH3:36])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:28]=[CH:27][C:26]([C:29]5[N:34]=[CH:33][C:32]([CH3:35])=[CH:31][N:30]=5)=[CH:25][CH:24]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1)(C(C)(C)C)(C)C.Cl>CO.O1CCOCC1>[CH3:36][C@@:10]1([CH2:9][OH:8])[S:16][CH2:15][CH2:14][N:13]2[C:17]([C:20]3([C:23]4[CH:24]=[CH:25][C:26]([C:29]5[N:34]=[CH:33][C:32]([CH3:35])=[CH:31][N:30]=5)=[CH:27][CH:28]=4)[CH2:22][CH2:21]3)=[N:18][N:19]=[C:12]2[CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86712921HCID 86712921, compound

Product 1

HCID 86712923HCID 86712923, compoundYield 79.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

The compound (348 mg, 0.67 mmol) obtained in Example 52-3) was dissolved in methanol (3 mL). A 4 N solution (1.67 mL) of hydrochloric acid in dioxane was added to the solution, and the mixture was stirred at room temperature for 1 h. The solvent was distilled off, the residue was dissolved in a mixed solvent of methylene chloride (50 mL) and methanol (2 mL), and the mixture was separated into organic and aqueous layers by the addition of saturated aqueous sodium hydrogencarbonate (20 mL). The organic layer was washed with saturated sodium chloride solution and then dried with anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=10% to 60%) to obtain the title compound (216 mg, 79%) in a white solid form.

Workup

  1. distillationThe solvent was distilled off
  2. dissolutionthe residue was dissolved in a mixed solvent of methylene chloride (50 mL) and methanol (2 mL)
  3. customthe mixture was separated into organic and aqueous layers
  4. additionby the addition of saturated aqueous sodium hydrogencarbonate (20 mL)
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=10% to 60%)

Sources & evidence

ORD record
ord-45aeb06194734641be77c5ef283c4e2b
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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