Pyridine → HCID 131710125, compound

HRID 1604921Notes

Reaction equation

HRID 1604921 reaction equation
[OH:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].N1C=CC=CC=1.[CH:43](F)=[O:44]>O1CCCC1>[CH:43]([O:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10])=[O:44]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15153Formyl fluoride2×HCID 390251HCID 390251, compound

Product 1

HCID 131710125HCID 131710125, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Diphenylmethyl 3-hydroxymethyl-7β-(2'-thienylacetamido)-ceph-3-em-4-carboxylate (3 g., 5.8 mmole.) and pyridine (6.5 ml., 82 mmole.) were dissolved in dry tetrahydrofuran (100 ml.), and cooled to -60°. A solution of formyl fluoride (~80 mmole.) in dry tetrahydrofuran (100 ml.), and cooled to -60°. A solution of formyl fluoride ( 80 mmole.) in dry tetrahydrofuran was added dropwise and the mixture maintained at -40° for 1 hour. On reaching room temperature, the mixture was filtered, concentrated, and partitioned between ethyl acetate and 2N-hydrochloric acid. On washing with more acid the ethyl acetate solution precipitated some product (1.77 g.); the remaining ethyl acetate was dried and evaporated to give more product (1.32 g.). A sample of the product was recrystallised from ethyl acetate, m.p. 189°, νmax (CHBr3), 1792 (β-lactam), 1730 and 1232 (COOR), 1690 and 1518 cm-1 (CONH). N.M.R. spectrum (dimethylsulphoxide) CHO at 179τ. (Found: C, 61.7; H, 4.4; N, 4.8. C28H24H2O6S2 requires C, 61.3; H, 4.4; N, 5.1%) NF = 0.7 (Kieselgel G plate, benzene:ethyl acetate = 2:1).

Workup

  1. temperaturecooled to -60°
  2. temperaturethe mixture maintained at -40° for 1 hour
  3. customOn reaching room temperature
  4. filtrationthe mixture was filtered
  5. concentrationconcentrated
  6. custompartitioned between ethyl acetate and 2N-hydrochloric acid
  7. washOn washing with more acid the ethyl acetate solution
  8. customprecipitated some product (1.77 g.)
  9. dry with materialthe remaining ethyl acetate was dried
  10. customevaporated
  11. customto give more product (1.32 g.)
  12. customA sample of the product was recrystallised from ethyl acetate, m.p. 189°, νmax (CHBr3), 1792 (β-lactam), 1730 and 1232 (COOR), 1690 and 1518 cm-1 (CONH)

Sources & evidence

ORD record
ord-86eae3622b1f473fac288fe232338fcb
Source dataset
uspto-grants-1976_04
Patent number
US03948906

Reaction notes

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