Sodium Hydroxide → HCID 178422683, compound

HRID 555266Notes

Reaction equation

HRID 555266 reaction equation
C([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([C:18]([N:20]3[CH2:26][C:25]4([CH3:28])[CH2:27][CH:21]3[CH2:22][C:23]([CH3:30])([CH3:29])[CH2:24]4)=[O:19])=[CH:17][C:11]=2[N:10]=1)=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:28][C:25]12[CH2:27][CH:21]([N:20]([C:18]([C:16]3[CH:15]=[CH:14][C:12]4[NH:13][C:9]([CH:7]5[CH2:8][CH:6]5[C:4]([OH:5])=[O:3])=[N:10][C:11]=4[CH:17]=3)=[O:19])[CH2:26]1)[CH2:22][C:23]([CH3:30])([CH3:29])[CH2:24]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178468463HCID 178468463, compound

Product 1

HCID 178422683HCID 178422683, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-[5-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-1H-benzimidazol-2-yl]-cyclopropanecarboxylic acid ethyl ester (60 mg, 0.147 mmol) in 96% ethanol (3 mL) at room temperature under an inert atmosphere of nitrogen was added 1N NaOH (aq) (0.36 mL, 0.36 mmol). The mixture was stirred for 16 hrs at 50° C. The reaction was quenched by the addition of water (3 mL) and acidified to pH 2 with 1N HCl followed by extraction with diethyl ether (2×5 mL). The combined organic phases were washed with water (2×5 mL), brine (5 mL), dried (MgSO4), filtered, and evaporated in vacuo affording 49 mg (88%) of the title compound as a solid. MS-ESI m/z 382; 1H NMR (400 MHz, CDCl3) δ 0.87-1.06 (m, 6H), 1.08-1.20 (m, 4H), 1.30-1.38 (m, 1H), 1.39-1.45 (m) and 1.48-1.64 (m, 3H), 1.70-1.90 (m, 2H), 1.91-2.01 (m, 1H), 2.18-2.30 (m) and 2.43-2.61 (m) and 2.85-3.02 (m, 2H), 3.15 (t) and 3.66 (t, 1H), 3.20-3.34 (m, 1H), 3.88-4.01 (m) and 4.54-4.65 (m, 1H), 7.39-7.50 (m, 1H), 7.69-7.85 (m, 2H).

Workup

  1. customThe reaction was quenched by the addition of water (3 mL)
  2. extractionfollowed by extraction with diethyl ether (2×5 mL)
  3. washThe combined organic phases were washed with water (2×5 mL), brine (5 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-be140c11d137423fa8728e4a5085fbda
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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