HCID 58355700, compound → HCID 58355350, compound

HRID 1184252Notes

Reaction equation

HRID 1184252 reaction equation
[OH:1][CH:2]([C@@H:4]1[CH2:9][C@H:8]([N:10]([C:15]([C:17]2[N:18]=[N:19][N:20]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[C:21]=2[CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)[CH3:3]>Cl.CO>[OH:1][CH:2]([C@H:4]1[CH2:5][NH:6][CH2:7][C@@H:8]([N:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:15]([C:17]2[N:18]=[N:19][N:20]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[C:21]=2[CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])=[O:16])[CH2:9]1)[CH3:3]

Participants

3

Reactant 1

HCID 58355700HCID 58355700, compound

Product 1

HCID 58355350HCID 58355350, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

tert-Butyl(3R,5S)-3-(1-hydroxyethyl)-5-[({5-[(2-methoxyethoxy)methyl]-1-(2-methylphenyl)-1H-1,2,3-triazol-4-yl}carbonyl)(2-methylpropyl)amino]piperidine-1-carboxylate (319 mg) was dissolved in 10% hydrogen chloride-methanol (4 ml), and the mixture was stirred at room temperature for 13 hr. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to reversed-phase preparative HPLC and the eluted fraction was concentrated under reduced pressure. The residual aqueous layer was neutralized with 3.5M aqueous potassium carbonate solution and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue and fumaric acid (27.9 mg) were dissolved in methanol (2 ml), and the solvent was evaporated under reduced pressure to give the object product (254 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationthe eluted fraction was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationthe solvent was concentrated under reduced pressure
  6. dissolutionThe residue and fumaric acid (27.9 mg) were dissolved in methanol (2 ml)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-dfae6875f97b4384b7e5ae57b525c6ec
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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