Sodium Hydroxide → HCID 58728079, compound

HRID 1992056Notes

Reaction equation

HRID 1992056 reaction equation
[CH3:1][C:2]1[N:6]([CH:7]2[CH2:13][C@H:12]3[N:14]([CH2:15][CH2:16][C:17]4([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH2:22][CH2:21][N:20]([C:23]([C:25]5([C:29]([O:31]CC)=[O:30])[CH2:28][CH2:27][CH2:26]5)=[O:24])[CH2:19][CH2:18]4)[C@H:9]([CH2:10][CH2:11]3)[CH2:8]2)[C:5]2[CH:40]=[CH:41][CH:42]=[CH:43][C:4]=2[N:3]=1.[OH-].[Na+]>C(O)C>[CH3:1][C:2]1[N:6]([CH:7]2[CH2:13][C@H:12]3[N:14]([CH2:15][CH2:16][C:17]4([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[CH2:22][CH2:21][N:20]([C:23]([C:25]5([C:29]([OH:31])=[O:30])[CH2:26][CH2:27][CH2:28]5)=[O:24])[CH2:19][CH2:18]4)[C@H:9]([CH2:10][CH2:11]3)[CH2:8]2)[C:5]2[CH:40]=[CH:41][CH:42]=[CH:43][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58727869HCID 58727869, compound

Product 1

HCID 58728079HCID 58728079, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 1-[(4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenylpiperidin-1-yl)carbonyl]cyclobutane-carboxylate from example 14 (0.050 g, 0.086 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 a white oil (0.032 g, 67%). 1H NMR (300 MHz, CDCl3) δ 7.68 (d, 1H), 7.27 (m, 8H), 4.63 (m, 1H), 3.84 (m, 1H), 3.41 (m, 1H), 3.25-2.95 (m, 4H), 2.87 (m, 1H), 2.58 (s, 3H), 2.45-2.20 (m, 4H), 2.05 (m, 2H), 1.89 (m, 8H), 1.63 (m, 5H), 1.61 (s, 2H). HRMS C34H42N4O3 m/z 555.3335 (M+H)Cal.; 555.3320 (M+H)Obs..

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-42dc7e06b98245479926673402124963
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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