HCID 46206527, compound → HCID 46206856, compound

HRID 1644733Notes

Reaction equation

HRID 1644733 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[C:5]2[C:16](=O)[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1.[H][H]>CO.[Pd].ClCCl>[CH3:26][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[CH:3]=3)[CH:8]=[C:7]([CH2:12][C:13]([OH:15])=[O:14])[CH:6]=2)=[CH:18][CH:19]=1)(=[O:24])=[O:25]

Participants

6

Reactant 2

HCID 46206527HCID 46206527, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 46206856HCID 46206856, compoundYield 21.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of [6-methyl-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid (example 2-28) (70 mg, 0.183 mmol) in methanol (8 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. After the reaction was complete (monitored by TLC, 4% methanol in dichloromethane), the solvent was evaporated in vacuo. Reverse-phase preparative HPLC (using a Waters® Delta-Prep™ 3000 with a Varian Pursuit® C-18 column [10 μm, 20×150 mm]) gave [4-(4-methanesulfonyl-benzyl)-6-methyl-naphthalen-2-yl]-acetic acid (14.4 mg, 21%) as a white solid. 1H NMR (300 MHz, CDCl3) δ ppm: 7.83 (d, J=8.4 Hz, 2 H), 7.74 (d, J=8.7 Hz, 1 H), 7.66 (s, 1H), 7.60 (s, 1 H), 7.38 (d, J=8.4 Hz, 2 H), 7.32 (d, J=8.7 Hz, 1 H), 7.22 (s, 1 H), 4.48 (s, 2 H), 3.78 (s, 2 H), 3.02 (s, 3 H), 2.46 (s, 3 H); HRMS cald. for O21H20O4S (ESI+) [(M+Na)+] 391.0974, obsd. 391.0976.

Workup

  1. customat 30° C.
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-07b1547c63744fae9f238a6385b74be7
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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