Methanol → HCID 131710596, compound

HRID 1414680Notes

Reaction equation

HRID 1414680 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:47](=[O:48])[N:12]2[C:13]([C:31]([O:33][CH:34]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])=[C:14]([NH:17]C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:15][S:16][C@H:11]12)=[O:8].C(Cl)Cl.CO.[H][H]>[Pd].C(O)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:47](=[O:48])[N:12]2[C:13]([C:31]([O:33][CH:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:32])=[C:14]([NH2:17])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 70636616HCID 70636616, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131710596HCID 131710596, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.178 g. (0.26 mmole) of benzhydryl 7-(2-thienylacetamido)-3-(4-nitrobenzyloxycarbonylamino)-3-cephem-4-carboxylate in 3 ml. of methylene chloride was combined with 70 ml. of methanol and 0.178 g. of 5 percent palladium on carbon (prereduced with hydrogen at 50 psi for 15 minutes) in 30 ml. of 3A ethanol. The alcoholic mixture was reduced with hydrogen at 50 psi for 3.5 hours. The catalyst was filtered and washed with hot 3A ethanol. The filtrate and washings were combined and evaporated in vacuo to dryness. A methylene chloride solution of the residue thereby obtained was filtered through a celite filter pad. Evaporation in vacuo to dryness provided 128 mg. (97.8 percent) of the title product as a yellow froth: ir (CHCl3) 1720 cm-1 (β-lactam); nmr (CDCl3) δ3.7 (ABq, C2--H), 3.92 (s, 1, side chain CH2), 5.01 (d, 1, J=4.0 Hz, C6--H), 5.32 (q, 1, J = 4.0 Hz, and 8.0 Hz, C7 --H), and 6.3 (NH).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with hot 3A ethanol
  3. customevaporated in vacuo to dryness
  4. customA methylene chloride solution of the residue thereby obtained
  5. filtrationwas filtered through a celite
  6. filtrationfilter pad
  7. customEvaporation in vacuo to dryness
  8. customprovided 128 mg

Sources & evidence

ORD record
ord-649f025e95794de1b1dd652225ed4a9a
Source dataset
uspto-grants-1977_01
Patent number
US04001226

Reaction notes

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