Sodium Hydroxide → HCID 20780285, compound

HRID 1293067Notes

Reaction equation

HRID 1293067 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[CH:13]1([CH2:16][N:17]([CH2:39][CH2:40][CH3:41])[C:18]([C:20]2[N:24]3[CH2:25][CH2:26][N:27]([C:28]4[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=4[CH3:36])[C:23]3=[N:22][C:21]=2[CH2:37]C)=O)[CH2:15][CH2:14]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:13]1([CH2:16][N:17]([CH2:18][C:20]2[N:24]3[CH2:25][CH2:26][N:27]([C:28]4[C:33]([CH3:34])=[CH:32][C:31]([CH3:35])=[CH:30][C:29]=4[CH3:36])[C:23]3=[N:22][C:21]=2[CH3:37])[CH2:39][CH2:40][CH3:41])[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 11502109HCID 11502109, compoundHCID 16684438Red-Al

Product 1

HCID 20780285HCID 20780285, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of Red-Al (3.3 M in toluene, 0.70 mL, 2.33 mmol) was added dropwise to a solution of 2-ethyl-7-(2,4,6-trimethyl-phenyl)-6,7-dihydro-5H-imidazo[1,2-α]imidazole-3-carboxylic acid cyclopropylmethyl-propyl-amide (0.177 g, 0.46 mmol) in toluene (3 mL) at 0° C. After stirring at room temperature for 24 h, the reaction mixture was cooled to 0° C. and I N sodium hydroxide (10 mL) was added dropwise. The above mixture was extracted with dichloromethane (40 mL), and the organic extracts were washed with water and dried over anhydrous sodium sulfate. Solvents were removed in vacuo to afford the title compound as a light yellow oil which solidified upon cooling (109 mg, 65% yield). The purity of the product was determined to be 91% by LC/MS. 1H NMR (CDCl3, 300 MHz) δ 6.85 (s, 2H), 4.09-3.96 (m, 4H), 3.45 (s, 2H), 2.44 (t, J=7.1 Hz, 2H), 2.29 (d, J=6.5 Hz, 2H), 2.23 (s, 3H), 2.19 (s, 6H), 2.04 (s, 3H), 1.46 (quintet, J=7.3 Hz, 2H), 1.28-1.25 (m, 1H), 0.87 (t, J=7.2 Hz, 3H), 0.49-0.46 (m, 2H), 0.09-0.06 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 155.4, 137.1, 136.9, 136.0, 135.0, 129.7, 117.7, 58.5, 55.5, 53.8, 48.0, 42.4, 20.9, 20.3, 18.2, 13.3, 12.0, 8.9, 4.0. Mass spec.: 367.24 (MH+).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. extractionThe above mixture was extracted with dichloromethane (40 mL)
  3. washthe organic extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customSolvents were removed in vacuo

Sources & evidence

ORD record
ord-af4fd6d87c924cc3862d28be9f96e034
Source dataset
uspto-grants-2007_07
Patent number
US07238699B2

Reaction notes

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