Pyrazole → HCID 131710130, compound

HRID 1604926Notes

Reaction equation

HRID 1604926 reaction equation
ClC(Cl)C(O[CH2:6][C:7]1[CH2:8][S:9][C@@H:10]2[C@H:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]3[S:22][CH:23]=[CH:24][CH:25]=3)[C:16](=[O:27])[N:11]2[C:12]=1[C:13]([OH:15])=[O:14])=O.[NH:29]1[CH:33]=[CH:32][CH:31]=[N:30]1>CC(C)=O>[N:29]1([CH2:6][C:7]2[CH2:8][S:9][C@@H:10]3[C@H:17]([NH:18][C:19](=[O:26])[CH2:20][C:21]4[S:22][CH:23]=[CH:24][CH:25]=4)[C:16](=[O:27])[N:11]3[C:12]=2[C:13]([OH:15])=[O:14])[CH:33]=[CH:32][CH:31]=[N:30]1

Participants

4

Reactant 2

HCID 1048PyrazoleHCID 131710126HCID 131710126, compound

Product 1

HCID 131710130HCID 131710130, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Dichloroacetoxymethyl-7β-(2'-thienylacetamido)ceph-3-em-4-carboxylic acid (3.2 g., 6.9 mmole.) was dissolved in 50%-aqueous acetone (60 ml.). and treated with pyrazole (1.6 g., 24 mmole.), and the solution heated at 50° for 35 minutes. The acetone was removed under reduced pressure, and the aqueous residue was extracted with ether (9 × 20 ml.). After drying, the ether was evaporated and the solid residue recrystallised from aqueous alcohol (1.3 g., 47%), mp. 180°-185° (decomp) [α]D30 = 53.5° (c 1.01, ethanol), λmax (ethanol) 236 nm. (β 14,000), 261 nm. (ε = 8,250) (shoulder), νmax (Nujol) 3272 (--NH), 1773 (β-lactam), 1712 (--COOH), 1660 and 1532 cm-1 (--CONH--). (Found: C, 50.9; H, 4.2; N, 13.9; S, 15.7. C17H16N4S2O4 requires C, 50.5; H, 4.0; N, 13.9; S, 15.9%). N.M.R. (D2O, with NaHCO3) 2.30, 3.62, 2.41τ (-N-CH=CH-CH=N), Rf 0.37 (Systems B), 0.12 (System C).

Workup

  1. temperaturethe solution heated at 50° for 35 minutes
  2. customThe acetone was removed under reduced pressure
  3. extractionthe aqueous residue was extracted with ether (9 × 20 ml.)
  4. customAfter drying
  5. customthe ether was evaporated
  6. customthe solid residue recrystallised from aqueous alcohol (1.3 g., 47%), mp. 180°-185° (decomp) [α]D30 = 53.5° (c 1.01, ethanol), λmax (ethanol) 236 nm

Sources & evidence

ORD record
ord-712c93469de3463c84a0fa9688948477
Source dataset
uspto-grants-1976_04
Patent number
US03948906

Reaction notes

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