3-(Chloromethyl)-5-phenyl-1,2,4-oxadiazole → HCID 54766234, compound

HRID 1044067Notes

Reaction equation

HRID 1044067 reaction equation
[C:1]1([C@@H:7]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:26][CH2:27][C:28]1[N:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:30][N:29]=1>CCOC(C)=O.C(#N)C>[Cl-:26].[C:33]1([C:31]2[O:30][N:29]=[C:28]([CH2:27][N+:13]34[CH2:14][CH2:15][CH:16]([CH2:17][CH2:18]3)[C@@H:11]([O:10][C:8](=[O:9])[C@@H:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:12]4)[N:32]=2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 3021543-(Chloromethyl)-5-phenyl-1,2,4-oxadiazoleHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

Product 1

HCID 54766234HCID 54766234, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)—((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate (diastereomer 1 of I2) (100 mg, 0.30 mmol) in EtOAc (2 ml) and acetonitrile (0.99 ml) was added 3-(chloromethyl)-5-phenyl-1,2,4-oxadiazole (I45) (69.4 mg, 0.36 mmol). The pale yellow solution was stirred at room temperature for 24 hours. The suspension was filtered on a buckner funnel washing with EtOAc (5 ml). The white solid was recovered from the filter to obtain the title compound (98 mg, 62.1% yield).

Workup

  1. filtrationThe suspension was filtered on a buckner funnel
  2. washwashing with EtOAc (5 ml)
  3. customThe white solid was recovered from the
  4. filtrationfilter

Sources & evidence

ORD record
ord-388f2917a1714a408fa9f687b5a0c6aa
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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