Hydrogen chloride-ethyl acetate → HCID 66892814, compound

HRID 1513616Notes

Reaction equation

HRID 1513616 reaction equation
[CH2:1]([N:3]([CH2:33][CH3:34])[CH2:4][CH2:5][N:6]([CH3:32])[C:7]([C:9]1[S:17][C:16]2[CH:15]=[C:14]([CH3:18])[N:13]([CH2:19][C:20](=[O:27])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12](=[O:28])[C:11]=2[C:10]=1[O:29][CH2:30][CH3:31])=[O:8])[CH3:2].C(OC(=O)C)C.[ClH:41]>C(OCC)(=O)C>[ClH:41].[CH2:33]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]([CH3:32])[C:7]([C:9]1[S:17][C:16]2[CH:15]=[C:14]([CH3:18])[N:13]([CH2:19][C:20](=[O:27])[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:12](=[O:28])[C:11]=2[C:10]=1[O:29][CH2:30][CH3:31])=[O:8])[CH3:34]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 57860518HCID 57860518, compound

Product 1

HCID 66892814HCID 66892814, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound of Example 146 (150 mg, 0.310 mmol) in ethyl acetate (20 mL) was added 4N hydrogen chloride ethyl acetate solution (93.0 μL, 0.372 mmol). The mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (30 mL) and ethanol (5 mL). Hexane (10 mL) was added, and the mixture was stirred at room temperature for 15 hr. The precipitated solid was collected by filtration, and washed with ethyl acetate to give the title compound (90.0 mg, 56%) as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  3. additionHexane (10 mL) was added
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-1c8f0e63bc3a44b0b154f07f147bddab
Source dataset
uspto-grants-2012_07
Patent number
US08217176B2

Reaction notes

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