p-Toluenesulfonic acid monohydrate → HCID 118362107, compound

HRID 2279983Notes

Reaction equation

HRID 2279983 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C@@H:10]([OH:30])[CH:11]([N:14]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]O)=[CH:4][CH:3]=1.O.[C:32]1([CH3:42])[CH:37]=CC(S(O)(=O)=O)=C[CH:33]=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C@@H:10]2[CH:11]([N:14]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:12][CH2:33][C:32]([CH3:42])([CH3:37])[O:30]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 118362103HCID 118362103, compound

Product 1

HCID 118362107HCID 118362107, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1,3-diol, 2-hydrazino (7C) (158 mg, 0.35 mmol) and p-toluene sulfonic acid monohydrate (6.8 mg, 0.035 mmol) in 10 mL anhydrous acetone was stirred at rt for 36 h, until the starting material was consumed as indicated by TLC (10:1/CH2Cl2/EtOAc). The reaction mixture was quenched with 5% NaHCO3 and extracted by CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4, and removed in vacuo. Purification by flash column chromatography on silica gel afforded the desired product as a white solid (93%).

Workup

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

Sources & evidence

ORD record
ord-7a9cccee10f846c9a2f75119c5816970
Source dataset
uspto-grants-2015_09
Patent number
US09133488B2

Reaction notes

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