Pyridine → Diphenylmethyl 3-acetoxymethyl-7beta-(2-benzoyloxyimino-2-phenylacetamido)-ceph-3-em-4-carboxylate

HRID 2398141Notes

Reaction equation

HRID 2398141 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:29]([NH:30][C:31](=[O:41])[C:32](=[N:39][OH:40])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:28](=[O:42])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])(=[O:3])[CH3:2].N1C=CC=CC=1.[C:49](Cl)(=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:29]([NH:30][C:31](=[O:41])[C:32](=[N:39][O:40][C:49](=[O:56])[C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:28](=[O:42])[N:10]2[C:11]=1[C:12]([O:14][CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 131710762Diphenylmethyl 3-acetoxymethyl-7beta-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylate

Product 1

HCID 131710761Diphenylmethyl 3-acetoxymethyl-7beta-(2-benzoyloxyimino-2-phenylacetamido)-ceph-3-em-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diphenylmethyl 3-acetoxymethyl-7β-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylate (1.0 g) and pyridine (1.5 ml.) in ethyl acetate (30 ml.) was added benzoyl chloride (1.5 ml.) and the mixture allowed to stand for one hour at room temperature. The solution was then washed with 2N-hydrochloric acid (50 ml.) and saturated brine, dried (sodium sulphate) and concentrated to ca. 5 ml. The concentrate was added dropwise to petroleum (b.p 40°-60°; 350 ml.) and the precipitated solid filtered, washed with petroleum and dried, yielding the title ester as a yellow solid (1.0 g; 85%), [α]D + 6.4° (c 0.94, DMSO), λmax. (EtOH) 259 nm (ε 26,700), νmax. (CHBr3) 1780 (β-lactam), 1640 and 1522 cm.-1 (CONH), τ (DMSO-d6) values include -0.27 (doublet J 8 Hz; NH), 1.8 - 2.8 (multiplet; aromatic protons), 8.01 (singlet; OCOCH3).

Workup

  1. washThe solution was then washed with 2N-hydrochloric acid (50 ml.) and saturated brine
  2. dry with materialdried (sodium sulphate)
  3. concentrationconcentrated to ca. 5 ml
  4. additionThe concentrate was added dropwise to petroleum (b.p 40°-60°; 350 ml.)
  5. filtrationthe precipitated solid filtered
  6. washwashed with petroleum
  7. customdried

Sources & evidence

ORD record
ord-14688c3daddb433cb267d27e14ac138c
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

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