Hydrogen chloride-ethyl acetate → HCID 67321805, compound

HRID 1509521Notes

Reaction equation

HRID 1509521 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]([N:19]([CH2:41][CH:42]([CH3:44])[CH3:43])[C@H:20]1[CH2:25][C@@H:24]([C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1)=[O:18].C(OCC)(=O)C.[ClH:51]>>[ClH:51].[ClH:51].[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:17]([N:19]([CH2:41][CH:42]([CH3:44])[CH3:43])[C@H:20]1[CH2:25][C@@H:24]([C:26]([N:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)=[O:27])[CH2:23][NH:22][CH2:21]1)=[O:18]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 58355528HCID 58355528, compound

Product 1

HCID 67321805HCID 67321805, compound

Procedure

tert-Butyl (3S,5R)-3-[{[1-(5-methoxypentyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (123 mg) was dissolved in 4M hydrogen chloride-ethyl acetate (5 ml), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated, and the residue was subjected to reversed-phase preparative HPLC and the eluted fraction was concentrated under reduced pressure. The residue was diluted with aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. 4M Hydrogen chloride-ethyl acetate (1 ml) was added and the mixture was stirred for 5 min. The solvent was evaporated under reduced pressure to give the object product (76 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. concentrationthe eluted fraction was concentrated under reduced pressure
  3. additionThe residue was diluted with aqueous sodium bicarbonate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. addition4M Hydrogen chloride-ethyl acetate (1 ml) was added
  8. stirringthe mixture was stirred for 5 min
  9. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-960ff692c3f540fb988f15c370ededd9
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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