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

HRID 2398142Notes

Reaction equation

HRID 2398142 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.[N+:49]([C:52]1[CH:60]=[CH:59][C:55]([C:56](Cl)=[O:57])=[CH:54][CH:53]=1)([O-:51])=[O:50]>C(OC(=O)C)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:56](=[O:57])[C:55]3[CH:54]=[CH:53][C:52]([N+:49]([O-:51])=[O:50])=[CH:60][CH:59]=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 85024-Nitrobenzoyl chlorideHCID 131710762Diphenylmethyl 3-acetoxymethyl-7beta-(2-hydroxyimino-2-phenylacetamido)ceph-3-em-4-carboxylate

Product 1

HCID 131710763Diphenylmethyl 3-acetoxymethyl-7beta-[2-(4-nitrobenzoyloxyimino)-2-phenylacetamido)ceph-3-em-4-carboxylateYield 66.1%

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 (synisomer) (1.5 g.) and pyridine (0.5 ml.) in ethylacetate (100 ml.) was added 4-nitrobenzoyl chloride (0.42 g) and the resulting solution was stirred at room temperature for one hour. Further portions (0.042 g 0.015 g and 0.20 g.) of the acid chloride were added, and the reaction stirred for a total of 4 hours at room temperature. Then the solution was washed with 2N-hydrochloric acid and brine, dried, concentrated to ca. 5 ml. and added dropwise with stirring to petroleum spirit (b.p. 40°-60° ). This gave a solid which was filtered and dried, yielding the title ester (1.1 g; 58%), λmax. (EtOH) 263 nm. (ε 29,000), νmax. (CHBr3) 3400 (NH), 1780 (β-lactam), 1395 an 1525 (NO2), 1687 and 1515 cm.- 1 (CONH), τ (CDCl3) values include 1.70 and 2.71 (two doublets, J 8 Hz; ##STR34## 2.1-2.85 (multiplet; aromatic protons), 8.03 (singlet; OCOCH3)

Workup

  1. stirringthe reaction stirred for a total of 4 hours at room temperature
  2. washThen the solution was washed with 2N-hydrochloric acid and brine
  3. customdried
  4. concentrationconcentrated to ca. 5 ml
  5. additionand added dropwise
  6. stirringwith stirring to petroleum spirit (b.p. 40°-60° )
  7. customThis gave a solid which
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-103c8629fd414431a3a8f56d249c9159
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

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