Pyridine → HCID 53632883, compound

HRID 329234Notes

Reaction equation

HRID 329234 reaction equation
C(Cl)(Cl)=O.[CH:5]([NH:7][C@@H:8]1[C:32](=[O:33])[N:10]2[C:11]([C:16]([O:18][CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])=[C:12]([CH3:15])[CH2:13][S:14][C@H:9]12)=O.N1C=CC=CC=1>C(Cl)Cl>[N+:7]([C@@H:8]1[C:32](=[O:33])[N:10]2[C:11]([C:16]([O:18][CH:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:17])=[C:12]([CH3:15])[CH2:13][S:14][C@H:9]12)#[C-:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 57240513HCID 57240513, compound

Product 1

HCID 53632883HCID 53632883, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of phosgene (3.27 g, 33 mmole) in methylene chloride (ca. 25 ml.) at -20° was added to a stirred solution of diphenylmethyl (6R, 7R)-7-formamido-3-methyl-ceph-3-em-4-carboxylate (prepared as described in Belgian Patent Specification No. 761,897) (12.24 g., 30 mmole) in methylene chloride (500 ml.) containing pyridine (12 ml., 150 mmole), at -20°. The solution was washed with water (2 × 250 ml.) and the organic layers combined with the methylene chloride backwash (250 ml.) of the aqueous layers, dried, and evaporated to a brown foam, which was then dissolved in ethyl acetate (100 to 150 ml.). This solution was added to petroleum-ether (b.p. 40° to 60°) to precipitate the product, which was isolated by filtration and dried to give the title compound as a pale-pink solid (9.539 g., 24.4 mmole, 81.5%); m.p. 117° - 118°; [α]D ± 0°; λmax. 252.5 nm (ε 7,030); λinf. 257,263.5 nm (ε 6,690; 6,480); νmax. 2150 (C=N), 1795 (azetidin-2-one), 1722 (CO2R), 1498, 752 and 735 cm.-1 ([C6H5 ]2CH); τ 2.40 to 2.80 (m, [C6H5 ]2CH), 3.04 (s, [C6H5 ]2CH), 4.88 (d, J 4.5 Hz, C7 -H), 5.10 (d, J 4.5 Hz, C6 -H), 6.69 (s, C2 -H2), 7.81 (s, C3 -CH3). (Found; C, 67.2; H, 4.8; N, 6.9; S, 8.1; C22H18N2O3S (390.4) requires: C, 67.6; H, 4.6; N, 7.2; S, 8.2%).

Workup

  1. customprepared
  2. customat -20°
  3. washThe solution was washed with water (2 × 250 ml.)
  4. customdried
  5. customevaporated to a brown foam, which
  6. dissolutionwas then dissolved in ethyl acetate (100 to 150 ml.)
  7. additionThis solution was added to petroleum-ether (b.p. 40° to 60°)
  8. customto precipitate the product
  9. customwhich was isolated by filtration
  10. customdried

Sources & evidence

ORD record
ord-4a6f1d66ef7f461db6ba07198fabe585
Source dataset
uspto-grants-1977_04
Patent number
US04020077

Reaction notes

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