p-Toluenesulfonic acid monohydrate → HCID 68461427, compound

HRID 507440Notes

Reaction equation

HRID 507440 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][S:8][CH:7]([CH2:10][C:11]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([C:18]([OH:20])=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:6]1)=[O:4].CC1C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][S:8][CH:7]2[CH2:10][C:11]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18](=[O:20])[N:6]12)=[O:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 68464125HCID 68464125, compound

Product 1

HCID 68461427HCID 68461427, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of compound 15 (3 g, 7.3 mmol) and p-TsOH.H2O (0.3 g, 1.6 mmol) in toluene (150 mL) was heated to reflux for 1 h. The solution was washed with NaHCO3 solution and brine, dried over Na2SO4. After concentration, the residue was purified by column chromatography on silica gel (PE: EA=10:1) to give compound 16 (660 mg, 23.1%). 1H NMR (400 MHz, CDCl3) δ1.41 (s, 9 H), 3.04-3.07 (m, 1 H), 3.24-3.37 (m, 1 H), 3.39-3.41 (m, 1 H), 3.48-3.50 (m, 1 H), 3.74 (s, 3 H), 5.04 (bs, 1 H), 5.25 (bs, 1 H), 5.42 (bs, 1 H), 7.31-7.40 (m, 3H), 7.53-7.54 (m, 2H). MS (M+): 393. The stereochemistry was identified by NOE experiment.

Workup

  1. temperatureto reflux for 1 h
  2. washThe solution was washed with NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentration
  5. customthe residue was purified by column chromatography on silica gel (PE: EA=10:1)

Sources & evidence

ORD record
ord-54ef9397a4da4fe8be7a34241a36f2b0
Source dataset
uspto-grants-2010_08
Patent number
US07786163B2

Reaction notes

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