Trifluoroacetic acid → HCID 131710418, compound

HRID 1282992Notes

Reaction equation

HRID 1282992 reaction equation
[C:1]([CH2:3][CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[C@H:28]([NH:29][C:30](=[O:37])[CH2:31][C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[C:27](=[O:38])[N:9]2[C:10]=1[C:11]([O:13]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:12])#[N:2].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[C:1]([CH2:3][CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[C@H:28]([NH:29][C:30](=[O:37])[CH2:31][C:32]3[S:33][CH:34]=[CH:35][CH:36]=3)[C:27](=[O:38])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])#[N:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131710419HCID 131710419, compound

Product 1

HCID 131710418HCID 131710418, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A solution of diphenylmethyl 3-(2-cyanoethyl)-7β-(2-thienylacetamido)ceph-3-em-4-carboxylate (1g.) in anisole (1 ml.) was treated with trifluoroacetic acid (4 ml.). After 5 minutes at 23° the solvents were removed in vacuo and the residue was partitioned between ethyl acetate and dilute aqueous sodium bicarbonate solution. The alkaline phase was washed thoroughly with ethyl acetate, then taken to pH2 with 2N-hydrochloric acid. The acidic mixture was extracted with ethyl acetate and the organic extracts washed with brine, and dried and evaporated in vacuo. The residual gum was dissolved in ethyl acetate and the solution run into petroleum ether to give, after filtration and drying, the title acid (567 mg., 82%) as an amorphous solid, m.p. ca 105° (decomp.) [α]D22 + 102° (C 0.75, 1% NaHCO3), λinflex. (0.1 M-pH 6 phosphate buffer) 260 nm. (ε 7,290), νmax. (Nujol) 3300 (NH), 3675 to 2400 (bonded OH), 2210 and 2250 (CN), 1775 (β-lactam), 1715 (CO2H), and 1665 and 1530 cm.-1 (CONH), τ (D2O with NaHCO3) 4.43 (C(7) --H, d, J 4.5 Hz), 4.95 (C(6) --H, d, J 4.5 Hz.), 6.13 (CH2CONH), 6.42 and 6.82 (C(2), AB-q, J 18 Hz.), and 7.1 to 7.6 (CH2CH2CN, ABCD-complex) (Found: C, 50.7; H, 4.0; N, 10.7; S, 16.0; C16H15N3O4S2 requires C, 50.9; H, 4.0; N, 11.1; S, 17.0%), Rf 0.28 (System C) and Rf 0.6 (System B).

Workup

  1. customAfter 5 minutes at 23° the solvents were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and dilute aqueous sodium bicarbonate solution
  3. washThe alkaline phase was washed thoroughly with ethyl acetate
  4. extractionThe acidic mixture was extracted with ethyl acetate
  5. washthe organic extracts washed with brine
  6. customdried
  7. customevaporated in vacuo
  8. dissolutionThe residual gum was dissolved in ethyl acetate
  9. customto give
  10. filtrationafter filtration
  11. customdrying
  12. customthe title acid (567 mg., 82%) as an amorphous solid, m.p. ca 105° (decomp.) [α]D22 + 102° (C 0.75, 1% NaHCO3), λinflex

Sources & evidence

ORD record
ord-5f9ddd72a92b4dc8a1d3524041728038
Source dataset
uspto-grants-1976_08
Patent number
US03974152

Reaction notes

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