Ammonium Chloride → HCID 58355462, compound

HRID 1260106Notes

Reaction equation

HRID 1260106 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[N:9][C:8]=1[C:18]([N:20]([CH2:40][CH:41]([CH3:43])[CH3:42])[C@H:21]1[CH2:26][C@@H:25]([C:27](=[O:32])N(OC)C)[CH2:24][N:23]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:22]1)=[O:19].[CH3:44][Mg]Br.[Cl-].[NH4+]>C1COCC1>[C:27]([C@@H:25]1[CH2:26][C@H:21]([N:20]([C:18]([C:8]2[N:9]=[N:10][N:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:7]=2[CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[O:19])[CH2:40][CH:41]([CH3:42])[CH3:43])[CH2:22][N:23]([C:33]([O:35][C:36]([CH3:37])([CH3:39])[CH3:38])=[O:34])[CH2:24]1)(=[O:32])[CH3:44]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 58355612HCID 58355612, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58355462HCID 58355462, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

tert-Butyl (3S,5R)-3-[{[5-(4-methoxybutyl)-1-phenyl-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]-5-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate (230 mg) was dissolved in THF (5 ml), a 1M solution (1.9 ml) of methylmagnesium bromide in THF was added at 0° C., and the mixture was stirred at room temperature for 2 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:5-1:2) was concentrated under reduced pressure to give the object product (177 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (1:5-1:2)
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-92d80fd597a747e39c2c4329ba1ce700
Source dataset
uspto-grants-2013_06
Patent number
US08466282B2

Reaction notes

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