Diphenylmethyl 3-[(5RS)-2,5-dihydro-2-oxofuran-5-yl methyl]-7beta-phenylacetamidoceph-3-em-4-carboxylate → Diphenylmethyl 3-[(5RS)-2-oxotetrahydrofuran-5-yl methyl]-7beta-phenylacetamidoceph-3-em-4-carboxylate

HRID 973874Notes

Reaction equation

HRID 973874 reaction equation
[O:1]=[C:2]1[CH:6]=[CH:5][CH:4]([CH2:7][C:8]2[CH2:9][S:10][C@@H:11]3[C@H:31]([NH:32][C:33](=[O:41])[CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:30](=[O:42])[N:12]3[C:13]=2[C:14]([O:16][CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[O:3]1>C(O)C.C1C=CC=CC=1.[Pd].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]2[CH2:9][S:10][C@@H:11]3[C@H:31]([NH:32][C:33](=[O:41])[CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:30](=[O:42])[N:12]3[C:13]=2[C:14]([O:16][CH:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:15])[O:3]1

Participants

5

Reactant 1

HCID 70366830Diphenylmethyl 3-[(5RS)-2,5-dihydro-2-oxofuran-5-yl methyl]-7beta-phenylacetamidoceph-3-em-4-carboxylate

Product 1

HCID 67923952Diphenylmethyl 3-[(5RS)-2-oxotetrahydrofuran-5-yl methyl]-7beta-phenylacetamidoceph-3-em-4-carboxylateYield 39.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 21965192Npc112006Solvent

Procedure

Diphenylmethyl 3-[(5RS)-2,5-dihydro-2-oxofuran-5-yl methyl]-7β-phenylacetamidoceph-3-em-4-carboxylate (Example 2(a)), (1.58 g) in 50% ethanol/benzene (100 mls) was treated with tris(triphenylphosphine)rhodium (I) chloride (0.75 g) and 10% palladium on carbon (0.2 g) and hydrogenated for several hours at room temperature. The reaction was monitored by t.l.c. analysis until formation of the slightly more polar product was complete. The solution was filtered through a small pad of silica gel and then concentrated. Purificationby `flash` chromatography afforded the title compound as a brown solid, (0.62 g, 39%); a sample recrystallized from ethyl acetate was shown to be a single isomer by spectroscopic analysis, m.p. 84°-89° C., νmax (KBr) 3400 (br), 3299, 1782, 1770, 1735, 1719, 1661, 1619, 1533, 1494, 1453 and 1373cm-1 ; δH (CDCl3) 1.75 (1H, m), 2.23 (2H, m), 2.43 (2H, m), 3.02 (1H, dd, J2.3, 13.8Hz), 3.52 (2H, ABq, J18.7Hz), 3.66 (2H, ABq, J16.2Hz), 4.66 (1H, m), 4.93 (1H, d, J4.7Hz), 5.87 (1H, dd, J4.7, 9.2Hz), 6.11 (1H, d, J9.2Hz), 6.84 (1H, s) and 7.25-7.5 (15H, m); [mass spectrum: +ve ion (3NOBA, Na+) MNa+ 605].

Workup

  1. filtrationThe solution was filtered through a small pad of silica gel
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-fd9498bef97d4a3282197b5e7e700553
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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