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(13) For ease of comparison, data representation formats were kept as closely as possible to HTE WG.
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(15) General Procedure used for acylation reaction: To three 4 mL vials each containing Boc‐L‐proline 3
(native solid, 1.9 % coated on glass beads and 4.5 % coated on polystyrene beads, 0.12 mmol, 1.0
equiv.) was added HATU (0.17 mmol, 1.5 equiv.), DIEA (0.23 mmol, 2.0 equiv.) and acetonitrile (0.1 M)
and allowed to shake using an orbital heater shaker for 5 min at 60°C, followed by addition of p‐
tolylmethanamine 4 (0.17 mmol, 1.5 equiv.) and allowed to shake overnight. Upon completion water
was added to the resulting mixture and extracted with ethyl acetate. The combined extracts were
dried down using Biotage® V‐10 and treated with TFA in methanol to remove the Boc group. The
crude product was dissolved in 1.5 mL DMSO/H2O (1:1), filtered, and the solid washed with additional
1.5 mL of DMSO. The crude product was purified using reverse phase preparative HPLC to yield pure
1
(S)‐N‐(4‐methylbenzyl)pyrrolidine‐2‐carboxamide 5 as a colorless oil. H NMR (400 MHz, CDCl3) δ:
8.36 (t, J = 5.7 Hz, 1H), 4.58 (d, J = 9.5 Hz, 1H), 4.33 (d, J = 5.8 Hz, 2H), 3.38 – 3.22 (m, 2H), 2.30 (s, 4H),
1.95 (pt, J = 9.0, 4.8 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ: 168.6, 137.2, 134.4, 129.3, 127.4, 59.6, 46.4,
43.6, 30.1, 24.4, 21.0.
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