For a registration in the database Chemotion, the information given below was retrieved and reworked from the publication: Synthesis of deuterated and fluorinated aromatic a,a‑disubstituted amino acid derivatives by Caroline E. Hartmann, Thomas Baumann, Michael Bächle and Stefan Bräse.https://doi.org/10.1016/j.tetasy.2010.04.026The following procedure was gained from the original publication (general procedure) and values in mg were taken from the experimental section. Information added in mmol and equiv. were recalculated and given as gained from the used material in mg. In a 10 mL vessel were placed 2-(2-(methyl-d3)phenyl)propanal (85.0 mg, 562 μmol, 1.00 equiv), L-Proline (2.00 mg, 17.4 μmol, 0.0309 equiv), chloramine-T (262 mg, 1.15 mmol, 2.05 equiv), 5 mL acetonitrile and a magnetic stir bar. The vessel was sealed with a septum, placed in a MW cavity, and locked with the pressure device. Constant microwave irradiation of 200 W as well as simultaneous air-cooling (0.7 bar, 10 psi) were used during the entire reaction time (30 min., 60 °C). After cooling to room temperature, the solvent was removed under reduced pressure, and the product was purified by column chromatography (diethyl ether/n-pentane) to afford the α-sulfamidated aldehyde as a colorless solid. Flash chromatography on silica with n-pentane/diethyl ether 2:1 delivered 4-methyl-N-(2-(2-(methyl-d3)phenyl)-1-oxopropan-2-yl)benzenesulfonamide (135 mg, 421 μmol, 75% yield) as a colorless solid.Analysis of the target compound: mp = 112°C. – Rf = 0.17 (n-pentane/diethylether 2:1). – 1H NMR (400 MHz, CDCl3): δ = 2.27 (s, 3 H, C4´TsCH3), 5.93 (bs, 1 H, NH), 6.98 (d, J = 8.2 Hz, 2 H, 3´´-HTs, 5´´-HTs), 7.05 (d, J = 7.6 Hz, 2 H, CHPh), 7.09–7.19 (m, 3 H, CHPh), 7.28 (d, J = 8.2 Hz, 2 H, 2´´-HTs, 6´´-HTs), 9.06 (s, 1 H, CHO) ppm. – 13C NMR (100 MHz, CDCl3): δ = 20.0 (CD3), 21.4 (C4´TsCH3), 66.7 (CCD3), 126.6 (C-4’), 127.5 (CTs-2’’, CTs-6’’), 128.6 (C-2’, C-6’), 128.8 (C-3’, C-5’), 129.2 (CTs-3’’, CTs-5’’), 134.1 (C-1’), 139.1 (CTs-1’’), 142.8 (CTs-4’’), 194.4 (CHO) ppm. – IR (KBr): v = 3254 (m), 3069 (w), 2951 (w), 2843 (w), 2727 (w), 1732 (m), 1599 (w), 1583 (w), 1495 (m), 1449 (m), 1405 (m), 1378 (w), 1329 (m), 1167 (m), 818 (m), 764 (m) cm–1. – FAB-MS: m/z (%): 277 (100) [M+], 155 (48) [C7H7SO2+], 91 (74) [C7H7+]. – HRMS (C16H14D3NO3S): calcd.: 307.1195, found: 307.1191. – C16H15D3NO3S (306.11 g/mol): calcd.: C 62.72, H 6.58, N 4.57, S 10.47, found: C 62.35, H 5.69, N 4.93, S 10.42.
