Styrene Oxide → HCID 59625181, compound

HRID 2192831Notes

Reaction equation

HRID 2192831 reaction equation
[NH2:1][C@@H:2]1[CH2:7][C@H:6]([N:8]([C:13]([C:15]2[C:16]([NH:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])=[N:17][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[N:19][CH:20]=2)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][N:4]([C:31]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:32])[CH2:3]1.[C:41]1([CH:47]2[CH2:49][O:48]2)[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.Cl([O-])(=O)(=O)=O.[Li+]>C(#N)C>[C:21]([C:18]1[N:17]=[C:16]([NH:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:15]([C:13]([N:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[C@H:6]2[CH2:7][C@@H:2]([NH:1][CH2:49][CH:47]([OH:48])[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH2:3][N:4]([C:31]([O:33][CH2:34][C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:32])[CH2:5]2)=[O:14])=[CH:20][N:19]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 7276Styrene OxideHCID 23665649Lithium perchlorateHCID 59625517HCID 59625517, compound

Product 1

HCID 59625181HCID 59625181, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl (3R,5S)-3-amino-5-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]piperidine-1-carboxylate (100 mg) and 2-phenyloxirane (55 μl) were dissolved in acetonitrile (5 ml), and lithium perchlorate (55 mg) was added. The mixture was stirred at room temperature for 3 days and thereafter stirred at 80° C. for 7 hr. The reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, eluted with ethyl acetate-hexane-methanol (10:90:0-100:0:0-85:0:15) and concentrated under reduced pressure to give the object compound (53.2 mg).

Workup

  1. stirringstirred at 80° C. for 7 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washeluted with ethyl acetate-hexane-methanol (10:90:0-100:0:0-85:0:15)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b9fd16f7d11432fbc6120362daaebd7
Source dataset
uspto-grants-2012_12
Patent number
US08329691B2

Reaction notes

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