Trifluoroacetic acid → HCID 178511763, compound

HRID 227148Notes

Reaction equation

HRID 227148 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:16]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([I:25])=[CH:24][C:18]=2[N:17]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[I:25][C:23]1[CH:22]=[CH:21][C:19]2[NH:20][C:16]([C@@H:8]([NH2:7])[CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[N:17][C:18]=2[CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454142HCID 178454142, compound

Product 1

HCID 178511763HCID 178511763, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (1.0 g, 2.16 mmol) in dichloromethane (11 mL) at 0° C. under an atmosphere of nitrogen was added trifluoroacetic acid (6.0 mL, 81 mmol) and the mixture stirred at 0° C. with warming to room temperature over 2 hours. The reaction mixture was concentrated in vacuo then basified with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate (2×25 mL). The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give (S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethylamine which was used in the subsequent step without further purification (750 mg, 96%).

Workup

  1. temperaturewith warming to room temperature over 2 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff1dff13a83d4da59f7e58c97b7fd761
Source dataset
uspto-grants-2009_07
Patent number
US07557221B2

Reaction notes

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