Piperidine → HCID 66924576, compound

HRID 1888204Notes

Reaction equation

HRID 1888204 reaction equation
C1C2C(O[C:15]([N:17](C)[C@@H:18]([CH3:49])[C:19]([NH:21][C:22]3[CH:48]=[CH:47][C:25]([CH2:26][C@@H:27]4[CH2:31][CH2:30][C@H:29]([C@H:32]([OH:39])[C:33]5[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=5)[N:28]4[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[CH:24][CH:23]=3)=[O:20])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>C1COCC1.ClCCl>[OH:39][C@H:32]([C:33]1[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=1)[C@H:29]1[CH2:30][CH2:31][C@@H:27]([CH2:26][C:25]2[CH:47]=[CH:48][C:22]([NH:21][C:19](=[O:20])[C@@H:18]([NH:17][CH3:15])[CH3:49])=[CH:23][CH:24]=2)[N:28]1[C:40]([O:42][C:43]([CH3:46])([CH3:44])[CH3:45])=[O:41]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 66924475HCID 66924475, compound

Product 1

HCID 66924576HCID 66924576, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.410 g (0.593 mmol) of tert-butyl(2S,5R)-2-[4-({(2S)-2-[[(9H-fluoren-9-yloxy)carbonyl](methyl)amino]propanoyl}amino)benzyl]-5-[(R)-hydroxy(pyridin-3-yl)methyl]pyrrolidine-1-carboxylate from step A in 3 mL of anhydrous THF was 0.152 g (1.78 mmol) of piperidine. The resulting mixture was stirred at ambient temperature for 24 h and then was diluted with 25 mL of dichloromethane. The mixture was washed with water then dried over magnesium sulfate. The mixture was filtered and evaporated to dryness in vacuo to afford the crude title compound which was used without further purification. LC-MS: m/z (ES) 469 (MH)+.

Workup

  1. washThe mixture was washed with water
  2. dry with materialthen dried over magnesium sulfate
  3. filtrationThe mixture was filtered
  4. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-b1f4b96184fc411c9bbfc375e4323114
Source dataset
uspto-grants-2013_08
Patent number
US08501786B2

Reaction notes

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