HCID 178454641, compound → HCID 178454640, compound

HRID 220308Notes

Reaction equation

HRID 220308 reaction equation
C([Si](C)(C)[O:6][C:7]1[C:12]2[NH:13][C:14]([CH2:16][CH2:17][CH2:18][N:19]([CH3:42])[CH2:20][CH2:21][C@:22]3([O:36][C:37](=[O:41])[CH:38]([CH3:40])[CH3:39])[CH2:27][C@H:26]4[CH2:28][CH2:29][C@@H:23]3[CH:24]=[C:25]4[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:15][C:11]=2[CH:10]=[CH:9][CH:8]=1)(C)(C)C>C1COCC1>[OH:6][C:7]1[C:12]2[NH:13][C:14]([CH2:16][CH2:17][CH2:18][N:19]([CH3:42])[CH2:20][CH2:21][C@:22]3([O:36][C:37](=[O:41])[CH:38]([CH3:39])[CH3:40])[CH2:27][C@H:26]4[CH2:28][CH2:29][C@@H:23]3[CH:24]=[C:25]4[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:15][C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

3

Reactant 1

HCID 178454641HCID 178454641, compound

Product 1

HCID 178454640HCID 178454640, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 287 mg of rac-isobutyric acid (1R*,2R*,4R*)-2-[2-({3-[7-(tert.-butyl-dimethyl-silanyloxy)-1H-benzoimidazol-2-yl]-propyl}-methyl-amino)-ethyl]-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester in 6 mL THF were added 73 mg of NEt3 trihydrofluoride. After stirring for 45 min the reaction was quenched by addition of sat. aq. NaHCO3. The mixture was extracted with EtOAc and the organic phase was dried over MgSO4. Concentration in vacuo and purification by CC with EtOAc-MeOH (2:1) yielded 131 mg of rac-isobutyric acid (1R*,2R*,4R*)-2-(2-{[3-(7-hydroxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester as yellow oil.

Workup

  1. customwas quenched by addition of sat. aq. NaHCO3
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe organic phase was dried over MgSO4
  4. concentrationConcentration
  5. customin vacuo and purification by CC with EtOAc-MeOH (2:1)

Sources & evidence

ORD record
ord-135c1c8adddc4c7d83a5786da3aca177
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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