HCID 59350853, compound → HCID 59350814, compound

HRID 1644756Notes

Reaction equation

HRID 1644756 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:14]=[C:13]([C:15](=[O:27])[C:16]2[CH:21]=[CH:20][C:19]([S:22](=[O:26])(=[O:25])[NH:23][CH3:24])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:28])[CH:11]=2)[CH:6]=1.[H][H].COC(=O)CC1C=C(CC2C=CC(S(=O)(=O)NC)=CC=2)C2C(=CC=C(F)C=2)C=1>CO.[Pd]>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:14]=[C:13]([CH:15]([OH:27])[C:16]2[CH:17]=[CH:18][C:19]([S:22](=[O:26])(=[O:25])[NH:23][CH3:24])=[CH:20][CH:21]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:28])[CH:11]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 59350853HCID 59350853, compoundHCID 66775000HCID 66775000, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59350814HCID 59350814, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of [6-fluoro-4-(4-methylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid methyl ester (prepared in an analogous manner to example 2-1) in methanol (20 mL) was hydrogenated using a H-cube hydrogenation reactor with a flow rate of 1 mL/min and a 10% palladium on carbon catalyst cartridge at 30° C. under 10 bar hydrogen pressure. The reaction gave a mixture of alcohol {6-fluoro-4-[hydroxy-(4-methylsulfamoyl-phenyl)-methyl]-naphthalen-2-yl}-acetic acid methyl ester and the corresponding fully hydrogenated product [6-fluoro-4-(4-methylsulfamoyl-benzyl)-naphthalen-2-yl]acetic acid methyl ester. Reverse-phase preparative HPLC (using a Waters® Delta-Prep™ 3000 with a Varian Pursuit® C-18 column [10 μm, 20×150 mm]) was used to separate these products, giving {6-fluoro-4-[hydroxy-(4-methylsulfamoyl-phenyl)-methyl]-naphthalen-2-yl}-acetic acid methyl ester (4.0 mg) as 3.0 mg of a white solid. MS cald. for C21H20FNO5S [(M−H)−] 417, obsd. 416.

Workup

  1. customat 30° C.
  2. customThe reaction gave
  3. customto separate these products

Sources & evidence

ORD record
ord-5c29085447bc4ca98ed0ab53574f8112
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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