p-Toluenesulfonic acid → HCID 86748549, compound

HRID 1608671Notes

Reaction equation

HRID 1608671 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][O:7][C:8]([C:10]1[C@@H:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:12]([C:18]([OH:20])=[O:19])=[C:13]([CH3:17])[NH:14][C:15]=1[CH3:16])=[O:9])(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:41]1[CH:46]=[CH:45][CH2:44][CH2:43][CH2:42]1>O1CCCC1.C(OCC)(=O)C>[C:1]([NH:4][CH2:5][CH2:6][O:7][C:8]([C:10]1[C@H:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:12]([C:18]([O:20][CH:42]2[CH2:43][CH2:44][CH2:45][CH2:46][O:41]2)=[O:19])=[C:13]([CH3:17])[NH:14][C:15]=1[CH3:16])=[O:9])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 70337867HCID 70337867, compound

Product 1

HCID 86748549HCID 86748549, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 36 mg of (4S)-5-(2-acetamidoethoxycarbonyl)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid in 0.5 ml of tetrahydrofuran were added 7.7 mg of p-toluenesulfonic acid, and then 0.24 ml of 3,4-dihydro-2-H-pyrane. The mixture was stirred at room temperature for 6 hours. The reaction mixture was diluted with 5 ml of ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and with water, and dried over anhydrous Glauber's salt (sodium sulfate), followed by distilling off the solvent under reduced pressure. The residue was purified using preparative TLC to obtain 18 mg of the objective compound.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution and with water
  2. dry with materialdried over anhydrous Glauber's salt (sodium sulfate)
  3. distillationby distilling off the solvent under reduced pressure
  4. customThe residue was purified

Sources & evidence

ORD record
ord-5fd356b6225c41b4bec6ef4c7281aaa7
Source dataset
uspto-grants-1995_03
Patent number
US05395941

Reaction notes

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