Water → Diisopropyl Ether

HRID 1591262Notes

Reaction equation

HRID 1591262 reaction equation
[C:1]([O:5]C([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[CH3:22])[CH2:14][S:15][C@H:10]12)=O)(C)([CH3:3])[CH3:2].O.[C:42]1([CH3:52])[CH:47]=CC(S(O)(=O)=O)=CC=1.O>C(#N)C.C(OCC)(=O)C>[NH2:8][CH:9]1[C:39](=[O:40])[N:11]2[C:12]([C:23]([O:25][CH:26]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:24])=[C:13]([C:16]3[C:19](=[O:20])[C:18](=[O:21])[C:17]=3[CH3:22])[CH2:14][S:15][C@H:10]12.[CH:1]([O:5][CH:42]([CH3:47])[CH3:52])([CH3:3])[CH3:2]

Participants

7

Reactant 3

HCID 962Water2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 88467566HCID 88467566, compound

Product 2

HCID 7914Diisopropyl EtherHCID 88467418HCID 88467418, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of diphenylmethyl 7-(t-butoxycarbonylamino)-3-(3,4-dioxo-2-methyl-1-cyclobutenyl)-3-cephem-4-carboxylate (100 mg, 0.178 mmol) and p-toluenesulfonic acid monohydrate (pTSOH.H2O, 68 mg, 0.357 mmol) in acetonitrile (0.5 mL) was stirred for 1 hr at 22° C. when additional pTSOH.H2O (34 mg, 0.178 mmol) was added. Stirring was continued for an additional 0.5 hr when the mixture was diluted with ethyl acetate. The solution was sequentially washed with dilute aqueous NaHCO3, H2O, and saturated NaCl. The solution was dried (Na2SO4) and concentrated. The residue was chromatographed on SiO2 (6 g) with methylene chloride/2-propanol (97:3) to provide the title compound as a yellow solid after trituration with diisopropyl ether.

Workup

  1. washThe solution was sequentially washed with dilute aqueous NaHCO3, H2O, and saturated NaCl
  2. dry with materialThe solution was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed on SiO2 (6 g) with methylene chloride/2-propanol (97:3)

Sources & evidence

ORD record
ord-9186db32366f40e382a396c57e084e69
Source dataset
uspto-grants-1993_04
Patent number
US05206360

Reaction notes

Loading…