4-Chloro-L-phenylalanine → 6-(5-((S)-2-Amino-3-(4-chlorophenyl)propylamino)-1,3,4-thiadiazol-2-yl)benzo[d]oxazol-2(3H)-one

Participants

Reaction Steps

The title compound was synthesized in a similar manner to that described for Example 11, by alkylating tert-butyl 5-(3-fluoro-4-nitrophenyl)-1,3,4-thiadiazol-2-ylcarbamate, prepared as in Example 1, with tert-butyl (4S)-4-(4-chlorobenzyl)-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide instead of tert-butyl (4S)-4-(4-(trifluoromethyl)benzyl)-1,2,3-oxathiazolidine-3-carboxylate 2-oxide. tert-Butyl (4S)-4-(4-chlorobenzyl)-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide was prepared as shown in Scheme 1b but using (S)-2-amino-3-(4-chlorophenyl)propanoic acid instead of (S)-2-amino-3-(4-(trifluoromethyl)phenyl)propanoic acid. LCMS (API-ES) m/z: 402 (M+H+); 1H NMR (400 MHz, CD3OD): δ ppm 2.95-3.07 (m, 2H), 3.55-3.60 (m, 1H), 3.70-3.75 (m, 1H), 3.80-3.86 (m, 1H), 7.17 (d, J=8 Hz, 1H), 7.33 (d, J=8 Hz, 2H), 7.40 (d, J=8 Hz, 2H), 7.59 (d, J=8 Hz, 1H), 7.69 (s, 1H).

Provenance & Evidence