Trifluoroacetic acid → HCID 66675068, compound

HRID 1176088Notes

Reaction equation

HRID 1176088 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:16]1[NH:17][C:18]([Br:21])=[CH:19][N:20]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C1(OC)C=CC=CC=1>[Br:21][C:18]1[NH:17][C:16]([C@@H:8]([NH2:7])[CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66938737HCID 66938737, compound

Product 1

HCID 66675068HCID 66675068, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Conditions

Temperature
100 °C

Procedure

[(S)-1-(5-bromo-1H-imidazol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester: To a solution of 92D (30 g) in anisole (100 mL) was added TFA (250 mL) and the reaction was stirred at 100° C. for 18 h. The reaction mixture was evaporated completely, basified with 5% NaOH solution and extracted with DCM. The organic layer was washed with brine, dried over sodium sulfate and concentrated. Recrystallization from hexane gave (S)-1-(5-bromo-1H-imidazol-2-yl)-2-phenyl-ethylamine as a white solid 6 (11 g, 67%). 1HNMR (CD3OD, 400 MHz), δ 7.26 (m, 3H), 7.06 (d, 2H), 6.96 (s, 1H), 4.18 (m, 1H), 3.09 (m, 2H). LCMS m/z 266 (M+H)+. To this intermediate (10 g, 37 mmol) in chloroform (250 mL) was added Boc anhydride (8.6 g, 39 mmol) dropwise at −15° C. over a period of 30 min. The reaction was warmed to 15° C. and stirred at the same temperature for 8 h. The reaction mixture was diluted with chloroform, washed with water and brine, dried over sodium sulfate and concentrated. The crude product was purified by recrystallisation from hexane to give 92E as an off-white solid (12.5 g, 91%). 1HNMR (CDCl3, 400 MHz), δ: 10.2 (bs, 1H), 7.3 (m, 5H), 7.15 (d, 2H), 6.85 (s, 1H), 5.34 (bs, 1H), 4.84 (m, 1H), 3.28 (dd, 2H), 1.38 (s, 9H). LCMS m/z 366 (M+H)+.

Workup

  1. customThe reaction mixture was evaporated completely
  2. extractionextracted with DCM
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customRecrystallization from hexane

Sources & evidence

ORD record
ord-41f6b967e4c442a0a39fa9d90d3ae1c2
Source dataset
uspto-grants-2010_11
Patent number
US07842708B2

Reaction notes

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