HCID 131710132, compound → HCID 131710131, compound

HRID 1604928Notes

Reaction equation

HRID 1604928 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[C@H:27]([NH:28][C:29](=[O:36])[CH2:30][C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)[C:26](=[O:37])[N:8]2[C:9]=1[C:10]([O:12]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:11]>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[CH3:1][O:2][CH2:3][C:4]1[CH2:5][S:6][C@@H:7]2[C@H:27]([NH:28][C:29](=[O:36])[CH2:30][C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)[C:26](=[O:37])[N:8]2[C:9]=1[C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 131710132HCID 131710132, compound

Product 1

HCID 131710131HCID 131710131, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

Diphenylmethyl 3-methoxymethyl-7β-(2'-thienylacetamido)-ceph-3-em-4-carboxylate (2 g.,) was dissolved in a mixture of trifluoroacetic acid (8 ml) and anisole (2 ml) and after 5 minutes the reagents removed under reduced pressure. The resulting gum was dissolved in ethyl acetate and poured into 60°-80° petroleum and the product recovered by filtration. This material crystallised from ethyl acetate as colourless prisms, m.p. 153°-157° (decomp.), [α]D25 + 81.6°(c 1, tetrahydrofuran), λmax (ethanol) 237, 260 (Sh.) nm (ε 13,700 and 7,700 respectively), νmax (Nujol) 1780 (β-latham), 1720 (-COOH), 1690 and 1524 cm-1 (-CONH), N.M.R. 5,80 (-CH2OCH3), 6.70τ (-CH2OCH3), (Found: C, 49.2; H, 4.4; N, 7.5; S, 17.0. C15H16N2O5S2 requires: C, 48.9; H, 4.4; N, 7.6; S, 17.4%).

Workup

  1. customremoved under reduced pressure
  2. dissolutionThe resulting gum was dissolved in ethyl acetate
  3. additionpoured into 60°-80° petroleum
  4. filtrationthe product recovered by filtration
  5. customThis material crystallised from ethyl acetate as colourless prisms, m.p. 153°-157° (decomp.), [α]D25 + 81.6°(c 1, tetrahydrofuran), λmax (ethanol) 237, 260 (Sh.) nm (ε 13,700 and 7,700 respectively), νmax (Nujol) 1780 (β-latham), 1720 (-COOH), 1690 and 1524 cm-1 (-CONH), N.M.R. 5,80 (-CH2OCH3), 6

Sources & evidence

ORD record
ord-9b37a4f86484422984ec151ee5b5a611
Source dataset
uspto-grants-1976_04
Patent number
US03948906

Reaction notes

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