Sodium Hydroxide → HCID 53261036, compound

HRID 1992186Notes

Reaction equation

HRID 1992186 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:24][CH2:25][N:26]3[C@H:31]4[CH2:32][CH2:33][C@@H:27]3[CH2:28][CH:29]([N:34]3[C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=5[N:36]=[C:35]3[CH3:43])[CH2:30]4)[CH2:13][CH2:12][N:11]([C:14](=[O:23])[C:15]([CH3:22])([CH3:21])[C:16]([O:18]CC)=[O:17])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:24][CH2:25][N:26]3[C@H:27]4[CH2:33][CH2:32][C@@H:31]3[CH2:30][CH:29]([N:34]3[C:38]5[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=5[N:36]=[C:35]3[CH3:43])[CH2:28]4)[CH2:13][CH2:12][N:11]([C:14](=[O:23])[C:15]([CH3:21])([CH3:22])[C:16]([OH:18])=[O:17])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58727760HCID 58727760, compound

Product 1

HCID 53261036HCID 53261036, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-(4-(3-fluorophenyl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-1-piperidinyl)-2,2-dimethyl-3-oxopropanoic acid was obtained from 3-Ethoxy-2,2-dimethyl-3-oxopropanoic acid, Example 628, (0.029 g, 0.18 mmol), 1-(8-(2-[4-(3-Fluoro-phenyl)-piperidin-4-yl]-ethyl)-8-aza-bicyclo[3.2.1]oct-3-yl)-2-methyl-1H-enzoimidazole dihydrochloride (0.075 g, 0.18 mmol), and HATU (0.067 g, 0.18 mmol) following the procedure outlined in example 5 to produce ethyl 3-(4-(3-fluorophenyl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-1-piperidinyl)-2,2-dimethyl-3-oxopropanoate. Ethyl 3-(4-(3-fluorophenyl)-4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-1-piperidinyl)-2,2-dimethyl-3-oxopropanoate (0.100 g, 0.170 mmol), 5 N NaOH (10 ml) and ethanol (4 ml) was stirred at 90° C. for 3 hrs. The reaction was evaporated to dryness and residue was suspend in water (10 ml) and neutralized with 1N HCl. The aqueous layer was extracted with ethyl acetate (3×10 ml). The organic layer was dried using magnesium sulfate and concentrated down to form the title compound as a white solid (0.081 g, 85%). ES-LCMS m/z 561 (M+1).

Workup

  1. customThe reaction was evaporated to dryness and residue
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×10 ml)
  3. customThe organic layer was dried
  4. concentrationconcentrated down

Sources & evidence

ORD record
ord-45e009f5f67a4140ba9c194aaef75f51
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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