Sodium Hydroxide → 3-[2-Ethyl-5-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-benzimidazol-1-yl]-propionic Acid

HRID 555264Notes

Reaction equation

HRID 555264 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16]([N:18]3[CH2:24][C:23]4([CH3:26])[CH2:25][CH:19]3[CH2:20][C:21]([CH3:28])([CH3:27])[CH2:22]4)=[O:17])=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:29][CH3:30])C.[OH-].[Na+]>C(O)C>[CH2:29]([C:8]1[N:7]([CH2:6][CH2:5][C:4]([OH:31])=[O:3])[C:11]2[CH:12]=[CH:13][C:14]([C:16]([N:18]3[CH2:24][C:23]4([CH3:26])[CH2:25][CH:19]3[CH2:20][C:21]([CH3:27])([CH3:28])[CH2:22]4)=[O:17])=[CH:15][C:10]=2[N:9]=1)[CH3:30]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 16723074HCID 16723074, compound

Product 1

HCID 167230753-[2-Ethyl-5-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-benzimidazol-1-yl]-propionic AcidYield 11.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-[2-ethyl-5-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)benzimidazol-1-yl]-propionic acid ethyl ester (104 mg, 0.244 mmol) in 96% ethanol (5 mL) at room temperature under an inert atmosphere of nitrogen was added 1N NaOH (aq) (0.3 mL, 0.3 mmol). The mixture was stirred for 2 hrs at room temperature. The reaction was quenched by the addition of water (5 mL) and acidified to pH 2 with 1N HCl followed by extraction with diethyl ether (2×10 mL). The combined organic phases were washed with water (2×10 mL), brine (10 mL), dried (MgSO4), filtered, and evaporated in vacuo affording 11 mg (11%) of the title compound as yellow oil. MS-ESI m/z 398; 1H NMR (400 MHz, CDCl3) δ 0.83-1.06 (m, 6H), 1.12-1.22 (m, 7H), 1.24-1.28 (m) and 1.46-1.54 (m, 1H), 1.30-1.39 (m, 2H), 1.33 (t, 3H), 1.63-1.74 (m, 1H), 2.22-2.32 (m) and 3.15-3.27 (m, 1H), 2.26 (t, 2H), 2.85 (t, 2H), 3.51 (q, 2H), 7.25-7.35 (m, 2H), 7.56 (d) and 7.74 (d, 1H).

Workup

  1. customThe reaction was quenched by the addition of water (5 mL)
  2. extractionfollowed by extraction with diethyl ether (2×10 mL)
  3. washThe combined organic phases were washed with water (2×10 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-be0ba1b9532f4003af94ca9ff9f9f037
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

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