Pyridine → HCID 58662612, compound

HRID 1181595Notes

Reaction equation

HRID 1181595 reaction equation
[CH:1]1([C@H:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[O:5][CH2:6][C@H:7]([OH:24])[CH2:8][NH:9][C:10]([CH3:23])([CH3:22])[CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[CH2:3][CH2:2]1.N1C=CC=CC=1.[C:38]1(=[O:44])[O:43][C:41](=[O:42])[CH:40]=[CH:39]1>C(Cl)(Cl)Cl>[CH:1]1([C@H:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[CH3:31])[O:5][CH2:6][C@H:7]([O:24][C:38](=[O:44])/[CH:39]=[CH:40]\[C:41]([OH:43])=[O:42])[CH2:8][NH:9][C:10]([CH3:23])([CH3:22])[CH2:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7923Maleic AnhydrideHCID 46871629HCID 46871629, compound

Product 1

HCID 58662612HCID 58662612, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(2R)-1-[(1R)-(Cyclopropyl)-(2-methylphenyl)methoxy]-3-[[2-methyl-1-(naphthalen-2-yl)propan-2-yl]amino]propan-2-ol (1.25g) was dissolved in chloroform (10 ml) and, under ice-cooling, pyridine (0.485 ml) and maleic anhydride (294 mg) were added and the mixture was stirred for 4 hr. The reaction mixture was concentrated under reduced pressure, and diethyl ether was added to the obtained residue. The organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=98:2-95:5) to give the title compound (1.40 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and diethyl ether
  3. additionwas added to the obtained residue
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=98:2-95:5)

Sources & evidence

ORD record
ord-825de858391f4b90b614f9b09bec8cc0
Source dataset
uspto-grants-2007_10
Patent number
US07285572B2

Reaction notes

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