HCID 57076211, compound → HCID 54291447, compound

HRID 861891Notes

Reaction equation

HRID 861891 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C@H:12]([CH:13]=[CH:14][C:15](=[O:21])[C@@H:16]3[CH2:20][CH2:19][CH2:18][O:17]3)[C@H:11]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10]2=[O:32])=[CH:5][CH:4]=1>O1CCCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C@H:12]([CH2:13][CH2:14][C:15](=[O:21])[C@@H:16]3[CH2:20][CH2:19][CH2:18][O:17]3)[C@H:11]([NH:22][C:23](=[O:31])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:10]2=[O:32])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 57076211HCID 57076211, compound

Product 1

HCID 54291447HCID 54291447, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3S,4R)-1-(4-methoxyphenyl)-4-[3-oxo-3-[(S)-tetrahydro-furan-2-yl]propenyl]-3-phenylacetamidoazetidin-2-one (12.1 g, 27.9 mmol) in tetrahydrofuran (250 ml) was hydrogenated over 10% palladium on carbon (1.0 g) for 3h. After filtration through celite, the partially insoluble product was dissolved in dichloromethane and methanol (1: 1) and re-filtered through celite to remove the catalyst. Concentration of the filtrate in vacuo provided the title compound as an amorphous white solid (11.5 g, 95%); (Found: M+ 436.1997. C25H27N2O5 requires M436.1998); νmax (KBr) 3277, 1758, 1708, 1655, 1542, 1510 and 1246 cm-1 ; δH (CDCl3) 1.43 (1H, m), 1.78-1.95 (3H, m), 2.10-2.50 (4H, m), 3.62 (2H, s), 3.75 (3H, s), 3.91 (2H, m), 4.17 (1H, m), 4.24 (1H, m), 5.29 (1H, dd, J 7.8, 5.0 Hz), 6.73 (1H, d, J 7.8 Hz, exch.), 6.81 (2H, d, J 9.0 Hz) and 7.25-7.36 (7H, m).

Workup

  1. filtrationAfter filtration through celite
  2. dissolutionthe partially insoluble product was dissolved in dichloromethane
  3. filtrationmethanol (1: 1) and re-filtered through celite
  4. customto remove the catalyst

Sources & evidence

ORD record
ord-eff0d293f1cb4d378dab2631ebe75daa
Source dataset
uspto-grants-1998_02
Patent number
US05716948

Reaction notes

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