Hydrogen chloride-ethyl acetate → HCID 67322036, compound

HRID 1184128Notes

Reaction equation

HRID 1184128 reaction equation
[F:1][C:2]1[C:7]2[N:8]([CH2:39][CH2:40][CH2:41][CH2:42][O:43][CH3:44])[C:9]([C:11]([N:13]([CH2:35][CH:36]([CH3:38])[CH3:37])[C@H:14]3[CH2:19][C@@H:18]([C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])[CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]3)=[O:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.[ClH:51]>>[ClH:51].[ClH:51].[F:1][C:2]1[C:7]2[N:8]([CH2:39][CH2:40][CH2:41][CH2:42][O:43][CH3:44])[C:9]([C:11]([N:13]([CH2:35][CH:36]([CH3:37])[CH3:38])[C@H:14]3[CH2:19][C@@H:18]([C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])[CH2:17][NH:16][CH2:15]3)=[O:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 58355214HCID 58355214, compound

Product 1

HCID 67322036HCID 67322036, compound

Procedure

tert-Butyl (3S,5R)-3-{{{7-fluoro-1-(4-methoxybutyl)-1H-benzimidazol-2-yl}carbonyl}(2-methylpropyl)amino}-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (160 mg) was dissolved in 2M hydrogen chloride-ethyl acetate (3 ml), and the mixture was stirred at room temperature for 10 hr. The reaction mixture was concentrated under reduced pressure. The residue was subjected to reversed-phase preparative HPLC, and a fraction eluted with water-acetonitrile (9:1-6:4) was collected, basified (pH 10) with saturated aqueous potassium carbonate solution, and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in 1M hydrogen chloride-ethyl acetate (1 ml), and the reaction mixture was concentrated under reduced pressure to give the object product (104 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washa fraction eluted with water-acetonitrile (9:1-6:4)
  3. customwas collected
  4. extractionextracted 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 1M hydrogen chloride-ethyl acetate (1 ml)
  8. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-661dd58ad0094fd38ed4598f4b4bc9b5
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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