Methanol → HCID 131711748, compound

HRID 2050340Notes

Reaction equation

HRID 2050340 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.CN(C)[C:9](=[O:11])[CH3:10].Br.[NH2:14][C@@H:15]1[C:41](=[O:42])[N:17]2[C:18]([C:25]([O:27][CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[C:19]([CH2:23][Br:24])[CH2:20][S@:21](=[O:22])[C@H:16]12.[CH3:43][OH:44]>ClCCl.C1OC1C>[Br:24][CH2:23][C:19]1[CH2:20][S@:21](=[O:22])[C@@H:16]2[C@H:15]([NH:14][C:25](=[O:26])[C:18]([C:19]3[O:11][CH:9]=[CH:10][CH:20]=3)=[N:17][O:44][CH3:43])[C:41](=[O:42])[N:17]2[C:18]=1[C:25]([O:27][CH:28]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[O:26]

Participants

7

Reactant 4

HCID 887MethanolHCID 24819Phosphorus pentachlorideHCID 31374DimethylacetamideHCID 131711749HCID 131711749, compound

Product 1

HCID 131711748HCID 131711748, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6378Propylene OxideSolvent

Procedure

To a solution of phosphorus pentachloride (3.7 g) in dried dichloromethane (40 ml) at -10° was added N,N-dimethylacetamide (8.25 ml.) and then, slowly, syn-2-(fur-2-yl)-2-methoxyiminoacetic acid (3.00 g), the temperature being kept at approximately -10°. The resulting solution was stirred for 15 minutes, then ice (9 g) was added and the temperature of the solution allowed to rise to 0° over 10 minutes. The organic layer was added to a stirred suspension of diphenylmethyl (1S,6R,7R)-7-amino-3-bromomethylceph-3-em-4-carboxylate 1-oxide, hydrobromide (7.34 g) in dried dichloromethane (100 ml) and propylene oxide (10 ml) at 0°. The reaction mixture was stirred for 45 minutes, during which time it was allowed to warm up to room temperature. To the resulting suspension was added methanol (60 ml) and this mixture was stirred for 10 minutes and then filtered. The white solid was washed with methanol and dried to give the title ester as a white microcrystalline powder (5.26 g, 64%), m.p. 186°-190° (decomp.); [α]D -4.5° (c 1.0, DMSO); λmax (EtOH) 281 nm (ε 22,600). IR and NMR spectroscopy confirmed the structure as that of the title ester.

Workup

  1. custombeing kept at approximately -10°
  2. waitto rise to 0° over 10 minutes
  3. stirringThe reaction mixture was stirred for 45 minutes, during which time it
  4. stirringthis mixture was stirred for 10 minutes
  5. filtrationfiltered
  6. washThe white solid was washed with methanol
  7. customdried

Sources & evidence

ORD record
ord-03113581973a4c3d9c847bdafeabe20d
Source dataset
uspto-grants-1980_04
Patent number
US04200746

Reaction notes

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