Tetrahydrofuran → HCID 57907534, compound

HRID 243730Notes

Reaction equation

HRID 243730 reaction equation
C1C2C(OC([N:17]([CH3:50])[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])C5C=NC=CC=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.N1[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]1.[CH2:57]1COCC1>ClCCl>[OH:39][C@H:32]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=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][CH3:50])[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 3

HCID 8028TetrahydrofuranHCID 8082PiperidineHCID 66924475HCID 66924475, compound

Product 1

HCID 57907534HCID 57907534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 above in 3 mL of anhydrous THF was added 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) 468 (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-dfee12fa6f214da596b69bea4b34fafb
Source dataset
uspto-grants-2014_02
Patent number
US08653260B2

Reaction notes

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