Acetic Anhydride → HCID 88801664, compound

HRID 1763805Notes

Reaction equation

HRID 1763805 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C@@H:9]1[C:25](=[O:26])[N:11]2[C:12]([C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])=[C:13]([CH3:16])[CH2:14][S:15][C@H:10]12>C(O)=O>[CH:1]([NH:8][C@@H:9]1[C:25](=[O:26])[N:11]2[C:12]([C:17]([O:19][CH2:20][C:21]([Cl:22])([Cl:24])[Cl:23])=[O:18])=[C:13]([CH3:16])[CH2:14][S:15][C@H:10]12)=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12266800HCID 12266800, compound

Product 1

HCID 88801664HCID 88801664, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Acetic anhydride (8 ml) was added to a solution of 2,2,2-trichloroethyl 7β-amino-3-methylceph-3-em-4-carboxylate (6.91 g, 20 mmole) in 98-100% formic acid (40 ml.), and the orange solution was allowed to stand at room temperature for 35 minutes and then successively evaporated at 30°/15 mm and 30°/1 mm. The orange residue was dissolved in ether (200 ml) and the solution was washed successively with 2N-hydrochloric acid, water and 5% aqueous sodium hydrogen carbonate solution (50 ml of each) and water (100 ml), dried and evaporated to give the title ester as a pale yellow foam (6.50 g, 87%), [α]D + 96° (CHCl3), λmax. 262-263 nm (E1cm1% 152), νmax. (CHBr3) 3400 (NH), 1786 (azetidin-2-one), 1740 (CO2R), and 1700 and 1510 cm-1 (CONH), τ (CDCl3) 1.74 (CHO), 7.79 (C3 -CH3) (Found: Cl, 27.5, 27.2; S, 8.2. C11H11Cl3N2O4S (373.7) requires Cl, 28.5; S, 8.6%).

Workup

  1. customsuccessively evaporated at 30°/15 mm and 30°/1 mm
  2. dissolutionThe orange residue was dissolved in ether (200 ml)
  3. washthe solution was washed successively with 2N-hydrochloric acid, water and 5% aqueous sodium hydrogen carbonate solution (50 ml of each) and water (100 ml)
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-1147f4af6d1744489b2959f2b38af271
Source dataset
uspto-grants-1978_09
Patent number
US04113591

Reaction notes

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