Hydrochloric Acid → HCID 135681855, compound

HRID 1354634Notes

Reaction equation

HRID 1354634 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(OC(C)(C)C)=O)[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>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[NH:15][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 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 23541917HCID 23541917, compound

Product 1

HCID 135681855HCID 135681855, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of sodium hydride (60% in oil, 0.003 g, 0.044 mmol) in toluene (1 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 (2 mL) over 5 minutes. The mixture was stirred at 90–100° C. for 5 hours, then cooled down to ˜0° C. and ethyl acetate followed by aqueous hydrochloric acid (1N, ˜0.5 mL) were added. The aqueous phase was washed with ethyl acetate (3×) and this was submitted to Prep HPLC (acetonitrile/ammonium acetate/water) to give the title material (0.008 g, 69%) as a white solid. HPLC 100% (220 nm); LCMS (+ESI, M+H+) m/z 315; 1H NMR (400 MHz, methanol-d4) δ (ppm): 2.55 (3H, s), 3.18 (4H, br dd), 3.81 (2H, s), 3.88 (4H, br dd), 6.92 (1H, br s), 6.99 (1H, d, J=2.0 Hz).

Workup

  1. additionwere added
  2. washThe aqueous phase was washed with ethyl acetate (3×)

Sources & evidence

ORD record
ord-1fcb617a38904a56a3e4628da24e2ab6
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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