Pyridine → HCID 18345144, compound

HRID 2301805Notes

Reaction equation

HRID 2301805 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][CH:23]([N:26]([C:29]([O:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:30])[CH2:27][CH3:28])[CH2:22][CH2:21]3)[CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:39](OC(=O)C)(=[O:41])[CH3:40].N1C=CC=CC=1>C(Cl)Cl>[C:39]([N:7]([CH:8]1[CH2:12][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([CH2:19][N:20]2[CH2:21][CH2:22][CH:23]([N:26]([C:29]([O:31][CH2:32][C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[O:30])[CH2:27][CH3:28])[CH2:24][CH2:25]2)[CH2:9]1)[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 86758765HCID 86758765, compound

Product 1

HCID 18345144HCID 18345144, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(RS and SR)-(cyclohexylamino)-3-(SR)-((4-(N-(benzyloxycarbonyl)-N-(ethyl)amino)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-7c170d8db7a947c09bfdccf18e9fd58e
Source dataset
uspto-grants-2002_12
Patent number
US06500844B1

Reaction notes

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