HCID 22246742, compound → HCID 22246768, compound

HRID 480270Notes

Reaction equation

HRID 480270 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[CH2:15][N:16]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>CO.[Pd].[C]>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([CH2:13][CH2:14][CH2:15][N:16]([S:26]([CH3:29])(=[O:28])=[O:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH:4]=[C:3]([C:2]([F:1])([F:30])[F:31])[CH:8]=1

Participants

4

Reactant 1

HCID 22246742HCID 22246742, compound

Product 1

HCID 22246768HCID 22246768, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A solution of trans-7-{[3-(3,5-bis-trifluoromethyl-phenyl)-allyl]-methanesulfonyl-amino}-heptanoic acid (210 mg, 0.44 mmol) in MeOH (10 mL) was added to 10% Pd/carbon (200 mg). The mixture was placed on a Parr hydrogenator at 50 psi and was hydrogenated for 20 h. The reaction was filtered through Celite with the aid of MeOH and the solvent was removed in vacuo. Purification by radial chromatography (2 mm rotary plate, 20:80:0.1 v/v/v EtOAc/hexanes/AcOH) provided the title compound (190 mg). 1H NMR (CDCl3 400 MHz) δ 7.69 (s, 1H), 7.63 (s, 2H), 3.20 (t, 2H), 3.14 (t, 2H), 2.81 (m, 5H), 2.28 (m, 2H), 1.94 (m, 2H), 1.32 (m, 4H); MS 495 (M+18).

Workup

  1. filtrationThe reaction was filtered through Celite with the aid of MeOH
  2. customthe solvent was removed in vacuo
  3. customPurification by radial chromatography (2 mm rotary plate, 20:80:0.1 v/v/v EtOAc/hexanes/AcOH)

Sources & evidence

ORD record
ord-8543bd0a494a48de8faaf426a79c294d
Source dataset
uspto-grants-2003_11
Patent number
US06649657B2

Reaction notes

Loading…