1,1-Dimethylethyl N-(aminosulfonyl)carbamate → 1,1-Dimethylethyl N-(aminosulfonyl)carbamate

Participants

Reaction Steps

N-t-butoxycarbonylsulfamide is prepared in the same manner as in the paragraph (a) of Step A-6 in Preparative Example 7-A. (2R,4R)-4-acetylthio-1-t-butoxycarbonylpyrrolidine-2-methanol (i.e., a substrate) is allowed to react with the obtained N-t-butoxycarbonylsulfamide in the similar manner as in paragraph (b) of Step A-6 in Preparative Example 7-A under a condition for Step B-6 shown in Table 2 to give (2R,4R)-4-acetylthio-1-t-butoxycarbonyl-2-(N-t-butoxycarbonyl-N-sulfamoylamino)methylpyrrolidine. NMR δ(CDCl3) ppm: 1.43(s, 9H), 1.53(s, 9H), 2.34(s, 3H), 2.5(m, 1H), 3.15(dd, J=12.2 Hz, J=6.2 Hz, 1H), 3.58(dd, J=14.8 Hz, J=3.2 Hz, 1H), 3.8 to 4.1(m, 2H), 4.16(dd, J=12.2 Hz, J=7.8 Hz, 1H), 4.4 to 4.7 (m, 1H), 6.11(s, 2H). IR ν (CHCl3) cm-1 : 3360, 3200, 1710, 1688.

Provenance & Evidence