HCID 7035943, compound → HCID 67923950, compound

HRID 973868Notes

Reaction equation

HRID 973868 reaction equation
[Br-].[CH3:2][C:3]1[CH:4]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:5](=[O:27])[O:6][C:7]=1[P+](C1CC=CCC=1)(C1CC=CCC=1)C1CC=CCC=1.[CH:34]([C:36]1[CH2:37][S:38][C@@H:39]2[C@H:59]([NH:60][C:61](=[O:69])[CH2:62][C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[C:58](=[O:70])[N:40]2[C:41]=1[C:42]([O:44][CH:45]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])=O>ClCCl.C(=O)([O-])O.[Na+]>[CH3:2][C:3]1=[C:4]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:5](=[O:27])[O:6]/[C:7]/1=[CH:34]/[C:36]1[CH2:37][S:38][C@@H:39]2[C@H:59]([NH:60][C:61](=[O:69])[CH2:62][C:63]3[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=3)[C:58](=[O:70])[N:40]2[C:41]=1[C:42]([O:44][CH:45]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43]

Participants

5

Reactant 2

HCID 7035943HCID 7035943, compoundHCID 67923954HCID 67923954, compound

Product 1

HCID 67923950HCID 67923950, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

2,5-Dihydro-4-methyl-2-oxo-3-phenylfuran-5-yl-triphenylphosphonium bromide (2.21 g) and diphenylmethyl 3-formyl-7β-phenylacetamidoceph-3-em-4-carboxylate (2 g) in dichloromethane (30 mls) and saturated aqueous sodium hydrogen carbonate (30 mls) were stirred vigorously atroom temperature for ca 20 mins. T.l.c. analysis showed all the starting material had been consumed. The organic layer was separated and washed with dilute hydrochloric acid, brine and then dried. After removal of solvent, the residue was flash chromatographed on silica gel eluting with 40% ethyl acetate/hexane. After trituration with ether, the title compound was obtained as a pale yellow crystalline compound, (0.643 g, 25%), m.p. 180°-183° C. (decomp.) ethyl acetate/hexane. (Found: C, 71.93; H, 5.10; N, 4.17; S, 4.54.%. C40H32N2O6S requires C, 71.84; H, 4.82; N, 4.19; S, 4.79%); νmax (CH2Cl2) 1785, 1760, 1715, 1680, 1490 and 1365cm - ; δH (CDCl3) 1.99 (3H,s), 3.44 (2H,ABq, J18.7Hz), 3.67 (2H,ABq,J16.1Hz), 5.02 (1H,d,J4.9Hz), 5.93 (1H,dd,J4.9,8.9Hz), 6.08(1H,d,J8.9Hz), 6.28(1H,s), 6.97 (1H,s) and 7.1-7.5 (20H,m); [mass spectrum: +ve ion (3-NOBA, Na+) MNa+, 691].

Workup

  1. customhad been consumed
  2. customThe organic layer was separated
  3. washwashed with dilute hydrochloric acid, brine
  4. customdried
  5. customAfter removal of solvent
  6. customchromatographed on silica gel eluting with 40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3e6aaed8f4b845c88376b187d800727a
Source dataset
uspto-grants-1991_11
Patent number
US05064649

Reaction notes

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