Hydrogen chloride-ethyl acetate → HCID 68434236, compound

HRID 2192853Notes

Reaction equation

HRID 2192853 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([CH2:38][CH:39]([CH3:41])[CH3:40])[C@H:20]2[CH2:25][C@@H:24]([C:26]([CH:28]3[CH2:30][CH2:29]3)=[O:27])[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(OCC)(=O)C.[ClH:48]>C(OCC)(=O)C>[ClH:48].[ClH:48].[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([C@H:20]2[CH2:25][C@@H:24]([C:26]([CH:28]3[CH2:29][CH2:30]3)=[O:27])[CH2:23][NH:22][CH2:21]2)[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:18])=[CH:7][N:6]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 59625278HCID 59625278, compound

Product 1

HCID 68434236HCID 68434236, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl (3S,5R)-3-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-(cyclopropylcarbonyl)piperidine-1-carboxylate (95 mg) was dissolved in ethyl acetate (3.2 ml), 4 M hydrogen chloride-ethyl acetate solution (0.8 ml) was added, and the mixture was stirred at room temperature for 16 hr. The solvent was evaporated under reduced pressure. The residue was subjected to reversed-phase preparative HPLC, and fractions eluted with water-acetonitrile (9:1) to acetonitrile were collected. The mixture was basified (pH 10) with saturated aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (5 ml), 4 M hydrogen chloride-ethyl acetate solution (75 μl) was added and the mixture was stirred for 1 min and concentrated under reduced pressure to give the object compound (48 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washeluted with water-acetonitrile (9:1) to acetonitrile
  3. customwere collected
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extract was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate (5 ml)
  8. addition4 M hydrogen chloride-ethyl acetate solution (75 μl) was added
  9. stirringthe mixture was stirred for 1 min
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d70055259f5645eea592aed670d66f10
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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