Hydrochloric Acid → HCID 178450553, compound

HRID 227151Notes

Reaction equation

HRID 227151 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:32][CH:31]=1)[C:9](=[O:29])[NH:10][C@H:11]([C:19]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([I:28])=[CH:27][C:21]=2[N:20]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(C)(C)C.Cl.O1CCOCC1>C(#N)C.O1CCOCC1>[NH2:7][C@H:8]([C:30]1[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[CH:34][CH:35]=1)[C:9]([NH:10][C@H:11]([C:19]1[NH:23][C:22]2[CH:24]=[CH:25][C:26]([I:28])=[CH:27][C:21]=2[N:20]=1)[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 178450554{(R)-[4-(2-tert-butoxy-ethoxy)-phenyl]-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

Product 1

HCID 178450553HCID 178450553, compound

Reagents, catalysts & solvents 1

HCID 22504236Acetonitrile dioxaneSolvent

Procedure

To a suspension of {(R)-[4-(2-tert-butoxy-ethoxy)-phenyl]-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (260 mg, 0.36 mmol) in 6:1 v/v acetonitrile/p-dioxane (14 mL) at 0° C. under an atmosphere of nitrogen was added 4.0 M hydrogen chloride in p-dioxane (420 μL, 1.68 mmol) and the resulting solution stirred at room temperature for 1 hour. Additional 4.0 M hydrogen chloride (420 μL, 1.68 mmol) was added and stirring continued for 30 minutes. The solvent was removed in vacuo and the residue was basified with saturated aqueous sodium hydrogen carbonate solution. The aqueous mixture was extracted with ethyl acetate (2×25 mL), washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give (R)-2-amino-2-[4-(2-tert-butoxy-ethoxy)-phenyl]-N-[(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-acetamide which was used in the subsequent step without further purification (210 mg, 94%).

Workup

  1. stirringstirring
  2. waitcontinued for 30 minutes
  3. customThe solvent was removed in vacuo
  4. extractionThe aqueous mixture was extracted with ethyl acetate (2×25 mL)
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d92e94b03eaf4cbc9f0cc11d7dc73084
Source dataset
uspto-grants-2009_07
Patent number
US07557221B2

Reaction notes

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