tert-Butyl 5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-ylcarbamate → 5-(5-((2S,3S)-2-Amino-3-(4-(trifluoromethyl)phenyl)butylamino)-1,3,4-thiadiazol-2-yl)indolin-2-one

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Reaction Steps

LCMS (API-ES) m/z (%): 448.1 (100%, M++H); 1H NMR (400 MHz, CD3OD) δ ppm 1.41 (d, J=7.03 Hz, 3H) 2.93-3.02 (m, 1H) 3.26-3.31 (m, 4H) 3.58-3.69 (m, 1H) 6.97 (d, J=8.53 Hz, 1H) 7.51 (d, J=8.03 Hz, 2H) 7.64 (t, J=7.28 Hz, 3H) 7.70 (s, 1H). The title compound was synthesized in a similar manner as Example 2 starting with tert-butyl (2S,3S)-1-(5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-yl-Boc-amino)-3-(4-(trifluoromethyl)phenyl)butan-2-ylcarbamate, which was synthesized in a similar manner to described for Example 1 using tert-butyl 5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-ylcarbamate to react with (S)-tert-butyl 4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)-1,2,3-oxathiazolidine-3-carboxylate, 2,2-dioxide. (S)-tert-Butyl 4-((S)-1-(4-(trifluoromethyl)phenyl)ethyl)-1,2,3-oxathiazolidine-3-carboxylate, 2,2-dioxide was synthesized as shown in Scheme 4.

Provenance & Evidence