HCID 67831555, compound → HCID 14654422, compound

HRID 981035Notes

Reaction equation

HRID 981035 reaction equation
C([NH:8][C:9]([C@H:11]1[CH2:14][C@@H:13]([C:15]([NH2:17])=[O:16])[NH:12]1)=[O:10])C1C=CC=CC=1>C(O)(=O)C.CO.[Pd]>[NH:12]1[C@H:13]([C:15]([NH2:17])=[O:16])[CH2:14][C@@H:11]1[C:9]([NH2:8])=[O:10]

Participants

5

Reactant 1

HCID 67831555HCID 67831555, compound

Product 1

HCID 14654422HCID 14654422, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

45.8 mg (196 μmol) of cis-N-benzylazetidine-2,4-dicarboxamide in 10 ml of glacial acetic acid (no reaction occurs in methanol) are hydrogenated in a Parr shaker over 11 mg of 10% Pd/C under a hydrogen pressure of 4 atm for 7 hours. The mixture is filtered through a fluted filter and the catalyst washed with several portions of methanol. Evaporation and drying in vacuo yields a colorless film which crystallizes slowly on addition of a few drops of methanol. After standing in a freezer overnight, the crystals are isolated, washed with a small volume of ethyl acetate/methanol (5:1), and dried in vacuo; yield 16.7 mg (60%). Mp. 215°-218° C. (dec.) after strong shrinking and darkening from approx. 200° C. on (measured with oil bath preheated to 190° C). 1H NMR (D2O): δ4.29 (t, 2H, J=8.5), 2.98 (dt, 1H, J=9 (t), 11 (d)), 2.23 (dt, 1H, J=8 (t), 11.5 (d)). IR (nujol): 3391, 3335, 3208, 3073, 1683, 1669, 1281, 1211, 1109, 1030, 843, 749, 722, 677 cm-1. Mass Spectrum: CI(isobutane): m/z 144 (M+H, 100%), 99 (56).

Workup

  1. customfor 7 hours
  2. filtrationThe mixture is filtered through
  3. filtrationa fluted filter
  4. washthe catalyst washed with several portions of methanol
  5. customEvaporation
  6. customdrying in vacuo
  7. customyields a colorless film which
  8. customcrystallizes slowly on addition of a few drops of methanol
  9. customthe crystals are isolated
  10. washwashed with a small volume of ethyl acetate/methanol (5:1)
  11. customdried in vacuo
  12. customdarkening from approx. 200° C. on (measured with oil bath preheated to 190° C)

Sources & evidence

ORD record
ord-fb092e3f751c484c89377c5c9c1f37da
Source dataset
uspto-grants-1991_02
Patent number
US04990504

Reaction notes

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