Methanol → HCID 42643645, compound

HRID 2283278Notes

Reaction equation

HRID 2283278 reaction equation
[C:1]1([C:6]2[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[S:14]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[S:24]([NH2:27])(=[O:26])=[O:25])(=[O:16])=[O:15])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1.CO.[H][H].C(OCC)(=O)C.CO>CCOC(C)=O>[CH:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][S:14]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[S:24]([NH2:27])(=[O:25])=[O:26])(=[O:15])=[O:16])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 21584119Ethylacetate methanolHCID 57750907HCID 57750907, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 42643645HCID 42643645, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(E)-2-(2-(4-Cyclopentenylphenyl)vinylsulfonamido)benzenesulfonamide (25.00 mg, 0.06 mmol) was dissolved in EtOAc (1.6 mL) and MeOH (1.6 mL) and hydrogenated under continuous flow hydrogenation conditions (full hydrogen, flow 1 ml/min, ethyl acetate/methanol 1:1 as eluent) at 50° C. using an H-Cube system. The solvent was removed in vacuo and the residue was purified by column chromatography on silica using heptane/ethyl acetate gradient mixtures as eluent (0-100% ethyl acetate) to give the product as a solid (14 mg, 55%).

Workup

  1. customat 50° C.
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-cdd407e390b04ea68844986d433155e3
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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