Chloroform → HCID 53785237, compound

HRID 597484Notes

Reaction equation

HRID 597484 reaction equation
[OH:1][C@@H:2]1[CH2:7][N:6]2[C:8](=[O:20])[C@@H:9]([NH:10][C:11](=[O:19])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:5]2[S:4][CH2:3]1.C(OC(=O)C)(=O)C.C(Cl)(Cl)Cl>CS(C)=O.C(OCC)(=O)C.C1C=CC=CC=1>[O:1]=[C:2]1[CH2:7][N:6]2[C:8](=[O:20])[C@@H:9]([NH:10][C:11](=[O:19])[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C@H:5]2[S:4][CH2:3]1

Participants

7

Reactant 3

HCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 54466737HCID 54466737, compound

Product 1

HCID 53785237HCID 53785237, compoundYield 23.8%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of (3R,6R,7R)-3-hydroxy-7-phenylacetamidocepham (1.4 g., 4.78 mmole) in dimethylsulphoxide (25 ml.) was added acetic anhydride (5 ml.). The reaction mixture was kept at 22° for 16 hours, diluted with ethyl acetate, and washed with water and sodium bicarbonate solution. Removal of the solvent gave a crystalline solid (1.23 g.) which was dissolved in benzene:ethyl acetate: chloroform = 2:2:1 (10 ml.) and adsorbed on a 10 × 2.5 cm column of silica gel. Elution with the same solvent mixture gave (6R,7R)-3-oxo-7-phenylacetamidocepham (0.33 g., 23%), as plates from isopropyl alcohol, m.p. 183.4° (Mettler), [α]D22 + 472.5° (c, 1.0, N,N-dimethylformamide), λmaxEtOH 250, 257, 263 nm (ε 280, 280, 190), νmaxnujol 3287 (NH), 1764 (β-lactam), 1712 (ketone), and 1650 and 1524 cm-1 (CONH), NMR (d6 -DMSO, τ) 0.85 (d, J 9 Hz, NH), 2.67 (C6H5), 4.61 (dd, J 4.5 and 9 Hz, 7-H), 4.86 (d, J 4 Hz, 6-H), 6.60 and 6.1 (q, J 19 Hz, 2-CH2), 6.10 and 6.86 (q, J 15 Hz, 4-CH2), 6.39 (Ph.CH2). (Found: C, 57.4; H, 4.9; N, 9.6; S, 10.9. C14H14N2O3S requires C, 57.9; H, 4.9; N, 9.6; S, 11.0%).

Workup

  1. washwashed with water and sodium bicarbonate solution
  2. customRemoval of the solvent
  3. customgave a crystalline solid (1.23 g.) which
  4. washElution with the same solvent mixture

Sources & evidence

ORD record
ord-3b8211944cd64ae38b4bd9d1cc1e2c27
Source dataset
uspto-grants-1977_03
Patent number
US04014872

Reaction notes

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