Trifluoroacetic acid → HCID 68131874, compound

HRID 259397Notes

Reaction equation

HRID 259397 reaction equation
FC(F)(F)C(O)=O.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][C:14]([NH:16][CH:17]1[C:48](=[O:49])[N:19]2[CH:20]([C:32]([O:34][CH:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[O:33])[C:21]([CH2:24][O:25]C(=O)CC(O)C)=[CH:22][S:23][C@H:18]12)=[O:15].S1[C@@H]2CC(=O)N2C=CC1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][C:14]([NH:16][CH:17]1[C:48](=[O:49])[N:19]2[CH:20]([C:32]([O:34][CH:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[O:33])[C:21]([CH2:24][OH:25])=[CH:22][S:23][C@H:18]12)=[O:15]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 208364673-Cephem2×HCID 131710854Benzhydryl 7-(2-thienylacetamido)-3-(3-hydroxybutanoyloxymethyl)-2-cephem-4-carboxylate

Product 1

HCID 68131874HCID 68131874, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 100 ml. of a solution of trifluoroacetic acid in methylene chloride (0.297 ml. trifluoroacetic acid in 125 ml. methylene chloride) at 0° C. was added 1.048 g. of a mixture of benzhydryl 7-(2-thienylacetamido)-3-(3-hydroxybutanoyloxymethyl)-2-cephem-4-carboxylate and the corresponding 3-cephem compound. After 6 hours a saturated aqueous sodium bicarbonate solution was added, and the mixture was allowed to warm to room temperature. The organic layer was separated, washed with saturated aqueous sodium chloride solution, dried over anhydrous MgSO4, and evaporated in vacuo to dryness. The foam thereby obtained was dissolved in methylene chloride; 59 mg. of 7-(2-thienylacetamido)-3-hydroxymethyl-3-cephem-4-carboxylic acid lactone (the product derived from the 3-cephem starting material) crystallized and was filtered. The filtrate was concentrated in vacuo and cooled. Another 209 mg. of lactone, mixed with some of the title product, was obtained. Evaporation in vacuo to dryness of the resulting solution provided 680 mg. of the title product: nmr (acetone D-6 ) δ3.85 (s, 2, side chain CH2), 4.17 (s, 2, --CH2OH), 5.25 (d, 1, J = 4.5 Hz, C6 --H), 5.54 (dd, 1, J = 4.5 and 8.0 Hz, C7 --H), 6.40 (bs, 1, C2 --H), 6.95 (s, 1, ester CH), 7.32 (m, 13, thienyl + ArH), and 8.04 (d, 1, J = 8.0 Hz, side chain NH).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated in vacuo to dryness
  5. customThe foam thereby obtained
  6. customcrystallized
  7. filtrationwas filtered
  8. concentrationThe filtrate was concentrated in vacuo
  9. temperaturecooled
  10. additionof lactone, mixed with some of the title product
  11. customwas obtained
  12. customEvaporation in vacuo to dryness of the resulting solution
  13. customprovided 680 mg

Sources & evidence

ORD record
ord-81f626b20a4e4a9b8e0cc9b24100197a
Source dataset
uspto-grants-1977_07
Patent number
US04038275

Reaction notes

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