HCID 68431882, compound → HCID 86074989, compound

HRID 1162815Notes

Reaction equation

HRID 1162815 reaction equation
C(OC([N:11]1[CH:17]2[CH:15]([CH:16]2[C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:14]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[C:13](=[O:31])[CH2:12]1)=O)C1C=CC=CC=1>[Pd].C(O)C>[F:30][C:27]1[CH:26]=[CH:25][C:24]([CH2:23][N:14]2[C:13](=[O:31])[CH2:12][NH:11][CH2:17][CH:15]2[CH2:16][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 68431882HCID 68431882, compound

Product 1

HCID 86074989HCID 86074989, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The lower Rf isomer of ethyl 5-benzyloxycarbonyl-2-(4-fluorobenzyl)-3-oxo-2,5-diazabicyclo[4.1.0]heptane-7-carboxylate (7.5 g, 17.5 mmol) and 10% palladium on carbon (940 mg; 0.05 mmol) in ethanol (200 mL) was stirred under an atmosphere of hydrogen (1 atm) at room temperature overnight. The product mixture was filtered through a pad of Celite, and concentrated under vacuum to provide the title compound. The structure was assigned by the analysis of HMQC, gHMBC and ROESY spectra. 1H NMR (400 MHz, CDCl3) δ 7.24 (dd, J=8.4, 5.3 Hz, 2H), 7.01 (t, J=8.6 Hz, 2H), 5.22 (d, J=15.0 Hz, 1H), 4.13 (q, J=7.2 Hz, 2H), 3.95 (d, J=14.8 Hz, 1H), 3.64-3.80 (m, 1H), 3.61 (d, J=4.5 Hz, 2H), 2.95-3.06 (m, 2H), 2.84 (dd, J=16.1, 9.4 Hz, 1H), 2.59 (dd, J=16.1, 2.4 Hz, 1H), 1.26 (t, J=7.2 Hz, 3H). ES MS (M+1)=295.32.

Workup

  1. filtrationThe product mixture was filtered through a pad of Celite
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-dfa9e285bdca44e3bfe95d39415d2657
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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