p-Toluenesulfonic acid monohydrate → HCID 57521313, compound

HRID 1746822Notes

Reaction equation

HRID 1746822 reaction equation
[OH:1][C@@H:2]([CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)/[CH:3]=[CH:4]/[C@@H:5]1[C@@H:13]2[C@@H:8]([S:9][C@@H:10]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:11][CH2:12]2)[CH2:7][C@H:6]1[O:21]C1CCCCO1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:21][C@@H:6]1[CH2:7][C@@H:8]2[S:9][C@@H:10]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:11][CH2:12][C@@H:13]2[C@H:5]1/[CH:4]=[CH:3]/[C@@H:2]([OH:1])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86702589HCID 86702589, compound

Product 1

HCID 57521313HCID 57521313, compoundYield 44.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound 13 (220 mg) was dissolved in methanol (1.1 mL), a p-toluenesulfonic acid monohydrate (20 mg) was added at room temperature, and the mixture was stirred for 2 hours. The residue obtained by concentration of the reaction liquid under reduced pressure was purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1→ethyl acetate) to obtain a titled compound (82 mg) having the following physical property values.

Workup

  1. customThe residue obtained by concentration of the reaction liquid under reduced pressure
  2. customwas purified by silica gel column chromatography (hexane:ethyl acetate=2:1→1:1→ethyl acetate)

Sources & evidence

ORD record
ord-381e2905c8fd4b89912ba0261d717481
Source dataset
uspto-grants-2015_10
Patent number
US09150537B2

Reaction notes

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