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

HRID 1707190Notes

Reaction equation

HRID 1707190 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 2 N-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 protens), 8.01 (singlet; OCOCH3) .

Workup

  1. washThe solution was then washed with 2 N-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-ce05cba2ddc54ac390528faef8a3e34a
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

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