[(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester → HCID 178454142, compound

HRID 227147Notes

Reaction equation

HRID 227147 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:16](=O)[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[NH2:25])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)N[C@H](C(=O)NC1C=C(I)C=CC=1N)CC1C=CC=CC=1)(C)(C)C>C(O)(=O)C>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:16]1[NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[N:25]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 66815065[(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl esterHCID 66815291[(S)-1-(2-amino-4-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 178454142HCID 178454142, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

The mixture of regioisomers from step 2 {[(S)-1-(2-amino-4-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester and [(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester} (1.0 g, 2.08 mmol) were dissolved in glacial acetic acid (30 mL) and heated to 65° C. for 1 hour. The reaction was cooled, concentrated in vacuo, basified with 10% w/v aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate (2×20 mL). The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel eluted with 20% v/v ethyl acetate/hexanes to give [(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester as a mixture of tautomers (950 mg, 99%).

Workup

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography over silica gel
  9. washeluted with 20% v/v ethyl acetate/hexanes

Sources & evidence

ORD record
ord-4132ae36f9d74e539886968456c5848c
Source dataset
uspto-grants-2009_07
Patent number
US07557221B2

Reaction notes

Loading…