Potassium Acetate → HCID 58125170, compound

HRID 403451Notes

Reaction equation

HRID 403451 reaction equation
[Si:1]([O:8][C@H:9]([C:32]1[CH:33]=[N:34][C:35](Cl)=[CH:36][CH:37]=1)[C@H:10]1[CH2:14][CH2:13][C@@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=2)[N:11]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])(=O)C.[K+]>[Pd].C(O)C>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][C@@H:12]2[CH2:13][CH2:14][C@H:10]([C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)[N:11]2[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 86650534HCID 86650534, compound

Product 1

HCID 58125170HCID 58125170, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 0.70 g (0.66 mmol) of 10% palladium on carbon was added a solution of 6.4 g (11 mmol) of tert-butyl(2R,5S)-2-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(6-chloropyridin-3-yl)methyl]-5-(4-nitrobenzyl)pyrrolidine-1-carboxylate from Step A above in 75 mL of anhydrous ethanol followed by 1.2 g (12 mmol) of potassium acetate. The resulting suspension was agitated under an atmosphere of hydrogen at 50 psi for 8 h. then filtered through a plug of Celite®. The plug was washed with ethanol (100 mL) and the combined filtrates were concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 40% ethyl acetate in hexanes to afford the title compound (i-8) as a colorless solid (0.31 g, 76%). LC-MS: m/z (ES) 498.4 (MH)+.

Workup

  1. filtrationthen filtered through a plug of Celite®
  2. washThe plug was washed with ethanol (100 mL)
  3. concentrationthe combined filtrates were concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-7d5fca86cdac4e25940c0a1ae722ebec
Source dataset
uspto-grants-2014_06
Patent number
US08748433B2

Reaction notes

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