Hydrochloric Acid → HCID 23109304, compound

HRID 1781997Notes

Reaction equation

HRID 1781997 reaction equation
[CH2:1]([N:5]1[C:9]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:8](=[O:15])[NH:7][C:6]1=[O:16])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].[C:23](OC([O-])=O)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].Cl>O>[CH2:1]([N:5]1[C:9]2([CH2:14][CH2:13][N:12]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:11][CH2:10]2)[C:8](=[O:15])[NH:7][C:6]1=[O:16])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 22064466Tert-butyldicarbonateHCID 23109294HCID 23109294, compound

Product 1

HCID 23109304HCID 23109304, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of the compound prepared in Example 5 (326 mg) in water (3 mL) were added potassium carbonate and t-butyl dicarbonate (348 mg) subsequently, and the mixture was stirred for 1 hour at room temperature. The reaction mixture was neutralized with 1N hydrochloric acid. The aqueous layer was extracted three times with ethyl acetate. The combined organic layer was washed with a saturated aqueous solution of sodium chloride, dried over an anhydrous magnesium sulfate and then concentrated. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1→1:2) to give the title compound (419 mg) having the following physical data.

Workup

  1. extractionThe aqueous layer was extracted three times with ethyl acetate
  2. washThe combined organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over an anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=5:1→1:2)

Sources & evidence

ORD record
ord-d47409756b99485191fa800c4bb3463b
Source dataset
uspto-grants-2009_03
Patent number
US07498323B2

Reaction notes

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