Water → Diisopropyl Ether

HRID 1030535Notes

Reaction equation

HRID 1030535 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 (6g) 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 (6g) with methylene chloride/2-propanol (97:3)

Sources & evidence

ORD record
ord-7789a62038584a988b70fe9e156444d7
Source dataset
uspto-grants-1992_04
Patent number
US05106842

Reaction notes

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