HCID 58355700, compound → HCID 58355350, compound

HRID 2169065Notes

Reaction equation

HRID 2169065 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-8bb2529923634e468b0e2b570a0c90ab
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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