Methanol → HCID 67923921, compound

HRID 973873Notes

Reaction equation

HRID 973873 reaction equation
[CH3:1][O:2][C:3]1=[C:4]([CH3:45])[C:5](=[O:44])[O:6]/[C:7]/1=[CH:8]/[C:9]1[CH2:10][S:11][C@@H:12]2[C@H:32]([NH:33]C(=O)CC3C=CC=CC=3)[C:31](=[O:43])[N:13]2[C:14]=1[C:15]([O:17][CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16].CN1CCOCC1.P(Cl)(Cl)(Cl)(Cl)Cl.CO>ClCCl.O>[NH2:33][C@@H:32]1[C:31](=[O:43])[N:13]2[C:14]([C:15]([O:17][CH:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])=[C:9](/[CH:8]=[C:7]3\[C:3]([O:2][CH3:1])=[C:4]([CH3:45])[C:5](=[O:44])[O:6]\3)[CH2:10][S:11][C@H:12]12

Participants

7

Reactant 4

HCID 887MethanolHCID 79724-MethylmorpholineHCID 24819Phosphorus pentachlorideHCID 67923934HCID 67923934, compound

Product 1

HCID 67923921HCID 67923921, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

Diphenylmethyl 3-(E-2,5-dihydro-4-methoxy-3-methyl-2-oxofuran-5-ylidenemethyl)-7β-phenylacetamidoceph-3-em-4-carboxylate (0.47 g), in dry dichloromethane (5 mls) was cooled to -20° C. under argon. This was treated with N-methylmorpholine (0.183 mls) and then a solution of phosphorous pentachloride in dichloromethane (5.13 mls, 40 mgs/ml). The solution was maintained at -20° C. for 30 mins and then methanol (5 mls) was added quickly, in one portion. The solution was allowed to warm to room temperature for a further 30 mins and water (10 mls) added. The reaction was vigorously stirred for 30 mins and then the dichloromethane removed in vacuo. The pH was adjusted to 7-8 with aqueous saturated sodium hydrogen carbonate and then extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated. `Flash` chromatography on silica gel, eluting with 80% ethyl acetate/hexane afforded the title compound as a yellow foam, (0.221 g, 58%), νmax (CH2Cl2) 3400(vw), 1760, 1720, 1625, 1490(w) and 1450(w) cm-1 ; δH (CDCl3) 1.94 (3H, s), 3.47 (2H, ABq, J18.2Hz), 3.87 (3H, s), 4.83 (1H, d, J5.1Hz), 4.98 (1H, d, J5.1Hz), 6.25 (1H, s), 7.00 (1H, s) and 7.2-7.5 (10H, m); [mass spectrum: +ve ion (3NOBA, Na+) MNa+, 527].

Workup

  1. temperatureto warm to room temperature for a further 30 mins
  2. customthe dichloromethane removed in vacuo
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. wash`Flash` chromatography on silica gel, eluting with 80% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a80c2b77636647f1a961926c0124add3
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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