Methanol → HCID 67908810, compound

HRID 467365Notes

Reaction equation

HRID 467365 reaction equation
[O:1]=[C:2]1[CH:6]=[C:5]([CH2:7][S:8][C:9]2[CH2:10][S:11][C@@H:12]3[C@H:32]([NH:33]C(=O)CC4C=CC=CC=4)[C:31](=[O:43])[N:13]3[C:14]=2[C:15]([O:17][CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:4][O:3]1.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:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])=[C:9]([S:8][CH2:7][C:5]3[CH2:4][O:3][C:2](=[O:1])[CH:6]=3)[CH2:10][S:11][C@H:12]12

Participants

7

Reactant 4

HCID 887MethanolHCID 79724-MethylmorpholineHCID 24819Phosphorus pentachlorideHCID 67908626HCID 67908626, compound

Product 1

HCID 67908810HCID 67908810, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of diphenylmethyl 3-(2,5-dihydro-2-oxofuran-4-ylmethylthio) -7β-phenylacetamidoceph-3-em-4-carboxylate (520 mg) in dry dichloromethane (8 ml) was cooled to -20° C., then N-methylmorpholine (0.202 ml) was added followed by a solution of phosphorous pentachloride in dichloromethane (7.2 ml of a solution containing 40 mg ml-1). The solution was stirred at -15° to -20° C. for 30 mins., then methanol (1.8 ml) was added and the mixture stirred at room temperature for 30 mins. Water (2.5 ml) was then added and the mixture vigorously stirred for a further 30 mins. The dichloromethane was then evaporated on a rotary evaporator and the residue partitioned between ethyl acetate and water. The pH of the aqueous phase was adjusted to 6.0 with saturated sodium bicarbonate solution and the organic phase was separated, washed with water, then brine, dried over magnesium sulphate and evaporated. The title compound (333 mg) was isolated by column chromatography of the residue (Kieselgel, ethyl acetate as eluent). υmax (CHCl3) 1780 and 1750 cm-1 ; δH (CDCl3) 1.86 (2H, broad s), 3.42 (1H, d, J 17.4Hz), 3.48 (1H, d, J 15.0Hz), 3.60 (1H, d, J 17.4Hz), 3.65 (1H, d, J 15.0Hz), 4.60 (2H, s), 4.78 (1H, d, J 5.1Hz), 4.95 (1H, d, J 5.1Hz), 5.89 (1H, s), 6.99 (1H, s), 7.2-7.5 (10H, m).

Workup

  1. stirringthe mixture stirred at room temperature for 30 mins
  2. stirringthe mixture vigorously stirred for a further 30 mins
  3. customThe dichloromethane was then evaporated on a rotary evaporator
  4. customthe residue partitioned between ethyl acetate and water
  5. customthe organic phase was separated
  6. washwashed with water
  7. dry with materialbrine, dried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-9e484a9f44064c0cbeaf92d38d531955
Source dataset
uspto-grants-1992_10
Patent number
US05158946

Reaction notes

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