p-Toluenesulfonic acid monohydrate → HCID 118362098, compound

HRID 2279982Notes

Reaction equation

HRID 2279982 reaction equation
[OH:1][CH2:2][CH:3]([N:15]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:4]([OH:14])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1.O.[C:32]1(C)[CH:37]=CC(S(O)(=O)=O)=C[CH:33]=1>CC(C)=O>[CH3:33][C:32]1([CH3:37])[O:14][C@H:4](/[CH:5]=[CH:6]/[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=2)[CH:3]([N:15]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:2][O:1]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 118362101HCID 118362101, compound

Product 1

HCID 118362098HCID 118362098, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1,3-diol, 2-hydrazino (7B) (59 mg, 0.14 mmol) and p-toluene sulfonic acid monohydrate (2.7 mg, 0.014 mmol) in 5.0 mL anhydrous acetone was stirred at rt for 42 h. The reaction mixture was quenched with 5% NaHCO3 and extracted with CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4, and removed in vacuo. Purification by flash chromatography on silica gel afforded the desired product as a white solid (94%).

Workup

  1. customThe reaction mixture was quenched with 5% NaHCO3
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. customremoved in vacuo
  5. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f9f84585b10944b6b7ba1266afda5f1a
Source dataset
uspto-grants-2015_09
Patent number
US09133488B2

Reaction notes

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