CarbaMic acid, N-[(1R)-1-[3-[6-(trifluoroMethyl)-1H-benziMidazol-2-yl]-5-isoxazolyl]ethyl]-, 1,1-diMethylethyl ester → 5-IsoxazoleMethanaMine, α-Methyl-3-[6-(trifluoroMethyl)-1H-benziMidazol-2-yl]-, (αR)-

HRID 2403145Notes

Reaction equation

HRID 2403145 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([C:11]3[CH:15]=[C:14]([C@H:16]([NH:18]C(=O)OC(C)(C)C)[CH3:17])[O:13][N:12]=3)[NH:8][C:7]=2[CH:26]=1>C(O)(C(F)(F)F)=O>[F:28][C:2]([F:1])([F:27])[C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([C:11]3[CH:15]=[C:14]([C@H:16]([NH2:18])[CH3:17])[O:13][N:12]=3)[NH:8][C:7]=2[CH:26]=1

Participants

3

Reactant 1

HCID 136088227CarbaMic acid, N-[(1R)-1-[3-[6-(trifluoroMethyl)-1H-benziMidazol-2-yl]-5-isoxazolyl]ethyl]-, 1,1-diMethylethyl ester

Product 1

HCID 1360881995-IsoxazoleMethanaMine, α-Methyl-3-[6-(trifluoroMethyl)-1H-benziMidazol-2-yl]-, (αR)-Yield 46.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of (R)-tert-butyl 1-(3-(6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)isoxazol-5-yl)ethylcarbamate (86.5 g, 0.22 mol) in TFA (300 mL) was stirred at RT for 2 hr. The reaction mixture was concentrated in vacuo and re-dissolved in ethyl acetate. The ethyl acetate solution was washed with K2CO3 and water, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography to afford compound Na, (R)-1-(3-(6-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)isoxazol-5-yl)ethanamine (30.2 g, 46.7%). 1H NMR (DMSO-d6) δ7.98 (s, 1H), 7.78 (d, 1H), 7.56 (d, 1H), 6.94 (s, 1H), 4.16 (q, 1H), 1.36 (d, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionre-dissolved in ethyl acetate
  3. washThe ethyl acetate solution was washed with K2CO3 and water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-5770e322a2714994b125707a587ca18c
Source dataset
uspto-grants-2014_08
Patent number
US08802657B2

Reaction notes

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