Sodium Hydroxide → HCID 20780285, compound

HRID 1295839Notes

Reaction equation

HRID 1295839 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:27][CH2:28][CH3:29])[C:6]([C:8]2[N:12]3[CH2:13][CH2:14][N:15]([C:16]4[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=4[CH3:24])[C:11]3=[N:10][C:9]=2[CH2:25]C)=O)[CH2:3][CH2:2]1.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH:1]1([CH2:4][N:5]([CH2:6][C:8]2[N:12]3[CH2:13][CH2:14][N:15]([C:16]4[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=4[CH3:24])[C:11]3=[N:10][C:9]=2[CH3:25])[CH2:27][CH2:28][CH3:29])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11502109HCID 11502109, compound

Product 1

HCID 20780285HCID 20780285, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of Red-A1 (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 (CDC13, 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-7a7744d32d7e4c7487fe50ee124633f6
Source dataset
uspto-grants-2007_07
Patent number
US07244746B2

Reaction notes

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