HCID 131710432, compound → HCID 54460561, compound

HRID 1390411Notes

Reaction equation

HRID 1390411 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S@@:8](=[O:34])[C@@H:9]2[C@H:20]([NH:21][C:22](=[O:32])[C:23]([C:27]3[O:28][CH:29]=[CH:30][CH:31]=3)=[N:24][O:25][CH3:26])[C:19](=[O:33])[N:10]2[C:11]=1[C:12]([O:14]C(C)(C)C)=[O:13])(=[O:3])[NH2:2]>FC(F)(F)C(O)=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S@@:8](=[O:34])[C@@H:9]2[C@H:20]([NH:21][C:22](=[O:32])[C:23]([C:27]3[O:28][CH:29]=[CH:30][CH:31]=3)=[N:24][O:25][CH3:26])[C:19](=[O:33])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[NH2:2]

Participants

3

Reactant 1

HCID 131710432HCID 131710432, compound

Product 1

HCID 54460561HCID 54460561, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

t-Butyl (1R,6R,7R)-3-carbamoyloxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylate 1-oxide (syn isomer) (0.42 g) was dissolved in trifluoroacetic acid (5 ml) and stirred at room temperature for 8 minutes. The solution was evaporated to a red oil in vacuo, dissolved in ethyl acetate:acetone (1:1, 5 ml) and added dropwise with stirring to petroleum ether (60°-80°, 50 ml). The deposited solid was collected and dried in a desiccator. The crude product was slurried with ethyl acetate, and the liquid phase was decanted and added dropwise to petroleum ether (60°-80°, 50 ml), yielding the title compound as a colourless solid (150 mg, 40%), λmax (0.25N NaHCO3) 263.5 (ε 15,000) and 281 nm (ε 13,700); νmax (Nujol) 1,799 (β-lactam), 1725 and 1716 (COOH and OCONH2), 1684 and 1538 (CONH) and 1060 and 1050 cm-1 (S→O); τ (Me2SO-d6) values include 0.02 (d, J8Hz, CONH), 4.17(dd, J4 and 8Hz, 7-H), 4.99 (d, J4Hz, 6-H) and 6.09 (s, N-OCH3).

Workup

  1. customThe solution was evaporated to a red oil in vacuo
  2. dissolutiondissolved in ethyl acetate:acetone (1:1, 5 ml)
  3. additionadded dropwise
  4. stirringwith stirring to petroleum ether (60°-80°, 50 ml)
  5. customThe deposited solid was collected
  6. customdried in a desiccator
  7. customthe liquid phase was decanted
  8. additionadded dropwise to petroleum ether (60°-80°, 50 ml)

Sources & evidence

ORD record
ord-a17ffe82fbfb4ba4a3df9370231f4bde
Source dataset
uspto-grants-1979_02
Patent number
US04138555

Reaction notes

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