p-Toluenesulfonic acid → HCID 89691331, compound

HRID 1054196Notes

Reaction equation

HRID 1054196 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:10]=[CH:9][O:8][C:7]=1[C:11]([N:13]1[C@@H:25]([C:26]([NH:28][CH3:29])=[O:27])[CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[CH2:14]1)=[O:12].CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH:2]([C:6]1[CH:10]=[CH:9][O:8][C:7]=1[C:11]([N:13]1[C@@H:25]([C:26]([NH:28][CH3:29])=[O:27])[CH2:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]=2[CH2:14]1)=[O:12])=[O:1]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 89698233HCID 89698233, compound

Product 1

HCID 89691331HCID 89691331, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of product (6-A) (2.2 g, 5.56 mmol) in acetone (20 ml) was added TsOH (191 mg, 1.11 mmol), and the solution was stirred at ambient temperature for 3 h. The reaction was quenched by saturated NaHCO3 (20 mL) and extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, and concentrated and purified by CC (DCM:MeOH=300:1 to 100:1) to give product (7-A) (1.8 g, 92%) as a brown solid. LC-MS (M+H)+=352.

Workup

  1. customThe reaction was quenched by saturated NaHCO3 (20 mL)
  2. extractionextracted with ethyl acetate (50 mL×2)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by CC (DCM:MeOH=300:1 to 100:1)

Sources & evidence

ORD record
ord-f528a9fbccd24465b48840865e5243ba
Source dataset
uspto-grants-2016_07
Patent number
US09394296B2

Reaction notes

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