FT-IR (cm ?1 ): 3314, 1709, 1655. MS/ESI: (M + H) + 253.0790 (m/z) Synthesis of (R)-4-Fluorophenyl-(3-oxoisoxazolidin-4-yl)- carbamate (1d). 1d was obtained as a white crystalline solid in 70% yield, mp 175?176 °C. 1 H NMR (DMSO-d 6 ): 11.54 (bs,1H, D 2 O exchange), = 8.56 Hz); 6.98 (d,2H, J = 8.56 Hz); 4.68?4.63 (m,1H), p.3916 ,
8 Hz); 154.1; 147.332 Hz); 116.5; 116.0 (d, J = 227 Hz); 72.0; 53.4. FT-IR (cm ?1 ): 3320, 1712, 1699 Synthesis of (R)-4-Bromophenyl-(3-oxoisoxazolidin-4-yl)- carbamate (1e). 1e was obtained as a white crystalline solid in 75% yield, mp 180?181 °C. 1 H NMR (DMSO-d 6 ): 11.55 (bs,1H, D 2 O exchange)42 (s, 1H, D 2 O exchange) General Procedure for Synthesis of Dicarbamates 2a?f. A 50 mg (0.5 mmol) portion of D-4-amino-3-isoxazolidinone were dissolved in 1.2 mL of aqueous 1 M NaHCO 3 and cooled at 0 °C, and 1.0 mmol of the corresponding chloroformate was added; the solution was stirred for 15 h. The obtained precipitates were collected by centrifugation, washed three times with 2 mL of water, and dried under reduced pressure to give compounds 2a?f subsequently crystallized from benzene, Synthesis of (R)-Phenyl-3-oxo-4-[(phenoxycarbonyl)- amino]isoxazolidine-2-carboxylate (2a). 2a was obtained as a white crystalline solid in 85% yield, mp 159?160. 1 H NMR (DMSO-d 6 ): 8.58 (bs, 1H, D 2 O exchange), pp.3-155, 1956. ,
Synthesis of (R)-4-Methylphenyl-4-{[(4-methylphenoxy)- carbonyl]amino}-3-oxoisoxazolidine-2-carboxylate (2b). 2b was obtained as a white crystalline solid in 75% yield, pp.914-922 ,
58 Hz); 5.02?4.95 (m, 1H), p.77 ,
1 H NMR (DMSO-d 6 ): 7.35 (s, 5H)06 (s, 2H); 4.87?4.80 (m, 1H), p.62 ,
77 Hz, J = 1.98 Hz)37 (m, 1H)30 Hz);7.24 (d, 2H); 5.15 (s, 2H), Hz, vol.7598787, issue.8, p.27979868 ,
Supporting Information Tables S1-S10 and Figures S1-S17. This material is available free of charge via the Internet at http ,
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