Heptane → HCID 88467540, compound

HRID 1591260Notes

Reaction equation

HRID 1591260 reaction equation
C(OC([NH:8][CH:9]1[C:39](=[O:40])[N:11]2[C:12]([C:23]([O:25][CH:26]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])=[C:13]([C:16]3[C:19](=[O:20])[C:18](=[O:21])[C:17]=3[NH2:22])[CH2:14][S:15][C@H:10]12)=O)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CCCCCCC>C(#N)C.O>[NH2:8][CH:9]1[C:39](=[O:40])[N:11]2[C:12]([C:23]([O:25][CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:24])=[C:13]([C:16]3[C:19](=[O:20])[C:18](=[O:21])[C:17]=3[NH2:22])[CH2:14][S:15][C@H:10]12

Participants

6

Reactant 3

HCID 8900HeptaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 88467426HCID 88467426, compound

Product 1

HCID 88467540HCID 88467540, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6342AcetonitrileSolvent2×

Procedure

Diphenylmethyl 7-(t-butoxycarbonylamino)-3-(2-amino-3,4-dioxo-1-cyclobutenyl)-3-cephem-4-carboxylate (400 mg, 0.712 mmol) was added to a stirred solution of p-toluenesulfonic acid monohydrate (272 mg, 1.43 mmols) in acetonitrile (1.6 mL). Stirring was continued for 0.5 hr at 22° C., at which time additional acetonitrile (1 mL) and H2O (2 drops) were added. Stirring was continued for an additional 0.5 hr at 22° C. and then for 0.33 hr at a water bath temperature of 35°-40° C. The solution was applied to a Michel-Miller HPLPLC column (22×300 mm, purchased from Ace Glass) containing Partisil Prep 40 ODS-3 (purchased from Whatman Chemical Separation Inc., Clifton, N.J.). The column was eluted with a mixture of 80% acetonitrile-20% H2O (50%) and 0.05M (pH 6.5) ammonium phosphate (50%). The appropriate fractions were combined and acetonitrile was removed on a rotary evaporator. The resulting mixture was extracted with ethyl acetate (3×). The combined extracts were washed (saturated aqueous NaCl), dried (MgSO4), and partially concentrated. Dilution with n-heptane precipitated the title compound as a yellow powder (93.6 mg, 28% yield). Analytical HPLC indicated a purity of 97 area percent.

Workup

  1. additionwere added
  2. stirringStirring
  3. waitfor 0.33 hr at a water bath temperature of 35°-40° C
  4. additioncontaining
  5. customPartisil Prep 40 ODS-3 (purchased from Whatman Chemical Separation Inc., Clifton, N.J.)
  6. washThe column was eluted with a mixture of 80% acetonitrile-20% H2O (50%) and 0.05M (pH 6.5) ammonium phosphate (50%)
  7. customacetonitrile was removed on a rotary evaporator
  8. extractionThe resulting mixture was extracted with ethyl acetate (3×)
  9. washThe combined extracts were washed (saturated aqueous NaCl)
  10. dry with materialdried (MgSO4)
  11. concentrationpartially concentrated

Sources & evidence

ORD record
ord-9809d1efa8554c2f921dfb11f1c21cc0
Source dataset
uspto-grants-1993_04
Patent number
US05206360

Reaction notes

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