Tetrahydrofuran → HCID 57907534, compound

HRID 887162Notes

Reaction equation

HRID 887162 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-6807f8602dda420aa7dad1338bf4c07a
Source dataset
uspto-grants-2012_08
Patent number
US08247415B2

Reaction notes

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