(5R)-3-[6-({5-[3-(Cyclopentylsulfonyl)phenyl]-4-pentyn-1-yl}oxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one → (5R)-3-[6-({5-[3-(Cyclopentylsulfonyl)phenyl]pentyl}oxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one

HRID 2118341Notes

Reaction equation

HRID 2118341 reaction equation
[CH:1]1([S:6]([C:9]2[CH:10]=[C:11]([C:15]#[C:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]3[CH2:31][C@@H:30]([C:32]4[CH:43]=[CH:42][C:35]5[O:36][C:37]([CH3:41])([CH3:40])[O:38][CH2:39][C:34]=5[CH:33]=4)[O:29][C:28]3=[O:44])[CH:12]=[CH:13][CH:14]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CCOC(C)=O.CCO.[Pt]=O>[CH:1]1([S:6]([C:9]2[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:27]3[CH2:31][C@@H:30]([C:32]4[CH:43]=[CH:42][C:35]5[O:36][C:37]([CH3:40])([CH3:41])[O:38][CH2:39][C:34]=5[CH:33]=4)[O:29][C:28]3=[O:44])[CH:12]=[CH:13][CH:14]=2)(=[O:7])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 2

HCID 69119922(5R)-3-[6-({5-[3-(Cyclopentylsulfonyl)phenyl]-4-pentyn-1-yl}oxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 69119698(5R)-3-[6-({5-[3-(Cyclopentylsulfonyl)phenyl]pentyl}oxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneYield 92.4%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (5R)-3-[6-({5-[3-(cyclopentylsulfonyl)phenyl]-4-pentyn-1-yl}oxy)hexyl]-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-one (215 mg) in EtOAc (10 ml) and EtOH (10 ml) was hydrogenated over platinum oxide (30 mg). When hydrogen uptake had ceased the mixture was filtered through celite and the solvent was evaporated in vacuo to give the title compound (200 mg). LCMS RT=3.83 min.

Workup

  1. filtrationwas filtered through celite
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-f2f674fec70246e0b92788b7ee45ea15
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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