Formic Acid → HCID 131710158, compound

HRID 1606520Notes

Reaction equation

HRID 1606520 reaction equation
[C:1]1([CH:7]([C:40]([O:42]C(C)(C)C)=[O:41])[C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([O:24]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:23])=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)=O.C(C(CCCC)C([O-])=O)C.[Na+:60].[Na][Na]>C(OCC)(=O)C.C(O)C>[Na+:60].[Na+:60].[C:1]1([CH:7]([C:40]([OH:42])=[O:41])[C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([O-:24])=[O:23])=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH:7]([C:40]([OH:42])=[O:41])[C:8]([NH:10][CH:11]2[C:38](=[O:39])[N:13]3[C:14]([C:22]([O-:24])=[O:23])=[C:15]([C:18]([O:20][CH3:21])=[O:19])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 141233DisodiumHCID 23672331Sodium 2-ethylhexanoateHCID 131710159HCID 131710159, compound

Product 1

HCID 131710158HCID 131710158, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzhydryl 7-(2-phenyl-2-tert-butoxycarbonylacetamido)-3-methoxycarbonyl-3-cephem-4-carboxylate (0.257 g., 0.399 mmol.) was dissolved in 40 ml. 97-100% formic acid and allowed to react for 1 hour at room temperature. The reaction mixture was evaporated to dryness to give a residue which was dissolved in ethyl acetate and extracted with sodium bicarbonate solution. The aqueous extracts were combined, layered with cold ethyl acetate, and acidified with cold 1N.HCl. The organic layer was separated, washed with brine and dried (Na2SO4). Evaporation to dryness gave 0.209 g. of acid which was dissolved in 40 ml. ethanol and treated with 2 equivalents of sodium 2-ethylhexanoate. The solution was evaporated in vacuo until a precipitate was noted. The solution was placed in the refrigerator overnight and filtered to give 27 mg. of the disodium salt: nmr (acetone-d6) 3.75 (m, 5, CO2CH3, C2 --H), 4.85 (2-s, 1, side chain CH), 5.17, 5.28 (2-d, 1, J = 5.0 Hz, C6 --H), and 5.92 ppm (q, 1, J = 5.0 Hz and 9.0 Hz, C7 --H).

Workup

  1. customto react for 1 hour at room temperature
  2. customThe reaction mixture was evaporated to dryness
  3. customto give a residue which
  4. extractionextracted with sodium bicarbonate solution
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customEvaporation to dryness
  9. customgave 0.209 g
  10. dissolutionof acid which was dissolved in 40 ml
  11. customThe solution was evaporated in vacuo until a precipitate
  12. customwas placed in the refrigerator overnight
  13. filtrationfiltered
  14. customto give 27 mg

Sources & evidence

ORD record
ord-bb62dc1a10734cc2a7e6d9505990d781
Source dataset
uspto-grants-1976_04
Patent number
US03953436

Reaction notes

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