Ethyl Acetate → HCID 135681558, compound

HRID 1354633Notes

Reaction equation

HRID 1354633 reaction equation
[H-].[Na+].C([O:5][C:6](=O)[CH2:7][NH:8][C:9](=[O:34])[CH2:10][C:11]1[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:14]2[CH:23]=[C:24]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:25]=[C:26]([CH3:27])[C:13]=2[N:12]=1)C.C(OCC)(=O)C.[Cl-].[NH4+]>C1(C)C=CC=CC=1.O1CCCC1>[OH:5][C:6]1[CH2:7][NH:8][C:9](=[O:34])[C:10]=1[C:11]1[N:15]([C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[C:14]2[CH:23]=[C:24]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[CH:25]=[C:26]([CH3:27])[C:13]=2[N:12]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 23541917HCID 23541917, compound

Product 1

HCID 135681558HCID 135681558, compoundYield 59.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of sodium hydride (60% in oil, 0.014 g, 0.352 mmol)in toluene (5 mL) was added [2-(1-tert-butyloxycarbonyl-4-methyl-6-morpholin-4-yl-1H-benzoimidazol-2-yl)-acetylamino]-acetic acid ethyl ester (0.135 g, 0.293 mmol) in tetrahydrofuran (5 mL) over 5 minutes. The mixture was stirred at 90–100° C. for 2.5 hours, then cooled down to ˜0° C. and ethyl acetate followed by aqueous ammonium chloride (˜3 mL) were added. The aqueous phase was extracted with ethyl acetate (3×). The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was quickly purified by silica gel chromatography to give the title material (0.072 g, 59%) as a white solid. LCMS (+ESI, M+H+) m/z 415, (− ESI, M−H−) m/z 413; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 1.47 (9H, s), 3.06 (4H, br s), 3.74 (4H, br s), 3.94 (2H, br s), 6.83 (1H, s), 6.97 (1H, s), 12.1 (1H, m), 12.56 (1H, s).

Workup

  1. additionwere added
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was quickly purified by silica gel chromatography

Sources & evidence

ORD record
ord-8116246729104196b388f97b236131b7
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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