Pyridine → HCID 86758890, compound

HRID 1862722Notes

Reaction equation

HRID 1862722 reaction equation
[CH:1]1([NH:7][CH:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]([CH2:19][N:20]3[CH2:25][CH2:24][C:23]([OH:35])([CH2:26][CH2:27][CH2:28][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:22][CH2:21]3)[CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:36](OC(=O)C)(=[O:38])[CH3:37].N1C=CC=CC=1>C(Cl)Cl>[C:36]([N:7]([CH:8]1[CH2:12][CH:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]([CH2:19][N:20]2[CH2:25][CH2:24][C:23]([OH:35])([CH2:26][CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:22][CH2:21]2)[CH2:9]1)[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86758891HCID 86758891, compound

Product 1

HCID 86758890HCID 86758890, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(RS and SR)-(cyclohexylamino)-3-(SR)-((4-hydroxy-4-(3-phenylprop-1-yl)piperidin-1-yl)methyl)-4-(SR)-phenylcyclopentane (prepared as in Example 43A) in methylene chloride (2 mL) was added acetic anhydride (0.17 mL, 1.67 mmol) and pyridine (0.17 mL, 2 mmol). The reaction was stirred at rt for 16 h. It was then diluted with methylene chloride and quenched with 1N NaOH. The mixture was washed with 1N NaOH and brine, dried over sodium sulfate and evaporated to dryness. The sample was purified by HPLC and the fractions containing the title compound by HPLC/MS were combined and evaporated.

Workup

  1. customquenched with 1N NaOH
  2. washThe mixture was washed with 1N NaOH and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness
  5. customThe sample was purified by HPLC
  6. additionthe fractions containing the title compound by HPLC/MS
  7. customevaporated

Sources & evidence

ORD record
ord-70f13a49d33c496494358fa185d5217e
Source dataset
uspto-grants-2003_03
Patent number
US06538002B1

Reaction notes

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