p-Toluenesulfonic acid monohydrate → HCID 131717299, compound

HRID 1681160Notes

Reaction equation

HRID 1681160 reaction equation
C(OC([NH:8][CH:9]1[C:42](=[O:43])[N:11]2[C:12]([C:26]([O:28][CH:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:13]([C:16]3[C:19](=[O:20])[C:18](=[O:21])[C:17]=3[O:22][CH:23]([CH3:25])[CH3:24])[CH2:14][S:15][C@H:10]12)=O)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[NH2:8][CH:9]1[C:42](=[O:43])[N:11]2[C:12]([C:26]([O:28][CH:29]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:27])=[C:13]([C:16]3[C:19](=[O:20])[C:18](=[O:21])[C:17]=3[O:22][CH:23]([CH3:24])[CH3:25])[CH2:14][S:15][C@H:10]12

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 131717298HCID 131717298, compound

Product 1

HCID 131717299HCID 131717299, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of diphenylmethyl 7-(t-butoxycarbonylamino)-3-(3,4-dioxo-2-(2-propoxy)-1-cyclobutenyl)-3-cephem-4-carboxylate (300 mg, 0.496 mmol) and p-toluenesulfonic acid monohydrate (189 mg, 0.992 mmol) in acetonitrile (1.5 mL) was stirred for 1 hr at 22° C. The solution was applied to the Michel-Miller HPLPLC column. The column was eluted with acetonitrile-H2O (45:55, v/v) to remove the toluenesulfonic acid and then with acetonitrile-H2O (70:30, v/v) to elute the deblocked amine. The acetonitrile was removed on a rotary evaporator and the resulting mixture extracted twice with ethyl acetate. The combined extracts were washed (saturated NaCl), dried (Na2SO4), and concentrated to leave the title compound (146 mg, 58% yield) as a yellow powder.

Workup

  1. washThe column was eluted with acetonitrile-H2O (45:55
  2. customv/v) to remove the toluenesulfonic acid
  3. washwith acetonitrile-H2O (70:30, v/v) to elute the deblocked amine
  4. customThe acetonitrile was removed on a rotary evaporator
  5. extractionthe resulting mixture extracted twice with ethyl acetate
  6. washThe combined extracts were washed (saturated NaCl)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-553cafadf109400b81be75579320d112
Source dataset
uspto-grants-1992_12
Patent number
US05169843

Reaction notes

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