HCID 21517622, compound → HCID 131710038, compound

HRID 1578878Notes

Reaction equation

HRID 1578878 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](=O)[CH2:10][S:11]([CH:13]2[N:16]([C:17]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=P(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:15](=[O:44])[CH:14]2[NH:45][C:46]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>O1CCOCC1>[C:1]1([CH2:7][CH2:8][C:9]2[CH2:10][S:11](=[O:12])[C@@H:13]3[CH:14]([NH:45][C:46]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)([C:59]4[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=4)[C:53]4[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=4)[C:15](=[O:44])[N:16]3[C:17]=2[C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 21517622HCID 21517622, compound

Product 1

HCID 131710038HCID 131710038, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(4-phenyl-2-oxobutylsulphinyl)-1-(1-t-butoxycarbonyl-1-triphenylphosphoranylidenemethyl)-3-(triphenylmethylamino) azetidin-2-one (200 mg) was refluxed in dry dioxan (5 ml) under nitrogen for 8 hours. The mixture was evaporated to give a foam. The crude foam was chromatographed on silica gel eluting with ethyl acetate/petroleum ether mixtures to give t-butyl 3-β-phenylethyl-7-triphenylmethylamino-3-cephem-4-carboxylate-1-oxide as a yellow solid (87 kg.) μmax (CHCl3) 1785, 1720 cm-1This sulphoxide (87 mg) was dissolved in dimethylformamide (1 ml) and cooled to 0°C. Triphenylphosphine (74 mg) and acetyl chloride (33 mg) were added and the mixture stood at 0°-5°C for 4 hours. The mixture was diluted with ethyl acetate (25 ml) and washed successively with dilute sodium bicarbonate solution and brine. The dried (MgSO4) organic layer was evaporated to give a gum. The gum was chromatographed on silica gel to give the desired cephem (XX111) as a solid foam (77 mg) νmax (CHCl3) 1775 cm-1 (ε-lactam); 1715 cm-1 (ester) δppm (CDCl3) 1.51 (5.9H); 2.4-3.2 (m.7H.1 H exchanges with D2O); 4.19 (d.1H. J=5Hz); 4.5-4.9 (m.1H); 7.0-7.9 (Aromatics).

Workup

  1. customThe mixture was evaporated
  2. customto give a foam
  3. customThe crude foam was chromatographed on silica gel eluting with ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-7a5c07b33c2d478bb0b01a236691a66e
Source dataset
uspto-grants-1976_02
Patent number
US03939157

Reaction notes

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