p-Toluenesulfonic acid monohydrate → Diisopropyl Ether

HRID 1681161Notes

Reaction equation

HRID 1681161 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>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

6

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrate2×HCID 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. additionwas added
  2. washThe solution was sequentially washed with dilute aqueous NaHCO3, H2O, and saturated NaCl
  3. dry with materialThe solution was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on SiO2 (6 g) with methylene chloride/2-propanol (97:3)

Sources & evidence

ORD record
ord-e5a83bcc96bf409c89e006903dc3e1da
Source dataset
uspto-grants-1992_12
Patent number
US05169843

Reaction notes

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