Trifluoroacetic acid → HCID 131711606, compound

HRID 261453Notes

Reaction equation

HRID 261453 reaction equation
[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[C@H:28]([NH:29][C:30](=[O:47])[CH2:31][CH:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]3=[N:38][O:39][CH2:40][C:41](C(C)(C)C)=[O:42])[C:27](=[O:48])[N:9]2[C:10]=1[C:11]([O:13]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:12])=[N+:2]=[N-:3].C1([O:55]C)C=CC=CC=1.FC(F)(F)C(O)=O>>[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[C@H:28]([NH:29][C:30](=[O:47])[CH2:31][CH:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]3=[N:38][O:39][CH2:40][C:41]([OH:42])=[O:55])[C:27](=[O:48])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])=[N+:2]=[N-:3]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131711607HCID 131711607, compound

Product 1

HCID 131711606HCID 131711606, compound

Procedure

Diphenylmethyl (6R,7R)-3-azidomethyl-7-(2-tertbutylcarbonylmethoxyiminophenylacetamido)-ceph-3-em-4-carboxylate (287 mg) was added to a mixture of anisole (0.3 ml) and trifluoroacetic acid (4 ml). The solution was stirred for 40 min. then evaporated. Benzene (50 ml) was added to the residue and removed by evaporation. The residue was partitioned between ethyl acetate and sodium bicarbonate solution; and the latter was acidified (10 N-HCl) under ethyl acetate, and extracted twice more with ethyl acetate. The organic extracts were washed with water and dried (Na2SO4), then evaporated, leaving an orange foam (183 mg). The foam was dissolved in ethyl acetate (2 ml) and added dropwise to vigorously stirred light petroleum (b.p. 40°-60°, 200 ml). Filtration gave the title-compound (100 mg, 51%), λmax (EtOH) 257.5 nm (ε 15,600), νmax (Nujol) 2100(N3), 1778(β-lactam), 1724(CO2H), 1670 and 1534 cm-1 (CONH), τ(Me2SO d6) values include 0.17(d, J=8 Hz; CONH), 2.2-2.7(Ph), 4.10 (C- 7H), 4.73(C-6H), 5.30(OCH2), 5.58 and 6.04(AB quartet, J=13 Hz, CH2N3), 6.29 and 6.52(AB quartet, J=18 Hz, SCH2).

Workup

  1. customthen evaporated
  2. additionBenzene (50 ml) was added to the residue
  3. customremoved by evaporation
  4. customThe residue was partitioned between ethyl acetate and sodium bicarbonate solution
  5. extractionextracted twice more with ethyl acetate
  6. washThe organic extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. customevaporated

Sources & evidence

ORD record
ord-471743735c7443298b538f0a991f53cb
Source dataset
uspto-grants-1979_08
Patent number
US04165430

Reaction notes

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