Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 114525-81-4, name is (R)-4-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows. 114525-81-4
(Scheme F, F-3: where RF-1 and RF-2 are the same and equal to proton, RF-3 is CH3, R5 is 4-[(2,6-dichlorobenzoyl)amino]phenyl and stereochemistry is (R,S)). [C00175] [00415] To a cooled (0 C.) solution of Boc-L-thiomorpholine-3-carboxylic acid ((a) Van Der Auwera, C.; Anteunis, M. J. O. Iit. J. Peptide Protein Res. 1987, 29, 574: (b) Kogami, Y.; Okawa, K. Bull. Chem. Soc. Jpn. 1987, 60, 2963: (c) Larsson U.; Carlson R. ACTA Chemica. Scand. 1994, 48, 517: (d) Carson J. F.; Wong F. F. J. Org. Chem. 1964, 29, 2203.) (Scheme F, F-1: where RF-1 and RF-2 are the same and equal to proton and stereochemistry is (R)) (6.7 g, 27 mmol) in CH2Cl2 (100 mL) was added HOBt (4.0 g, 29.7 mmol), DMAP (700 mg), EDC (5.7 g, 29.7 mmol) and triethylamine (13.5 mL, 97 mmol). The reaction mixture was stirred for 10 min, then the amino acid derivative F-2 (Scheme F, where R5 is 4-[(2,6-dichlorobenzoyl)amino]phenyl, RF-3 is CH3, and stereochemistry is (S)) (10.0 g, 24.7 mmol) was added. After 20 h, volatiles were removed in vacuo and the residue partitioned between 2.5% aqueous HCl (100 mL) and H2O (100 mL). The organic layer was separated and washed saturated aqueous NaHCO3 (100 mL), dried and concentrated in vacuo. Purification of the residue by chromatography on SiO2 (500 g) using CH2Cl2/ethyl acetate (10%) as eluent afforded the title compound (12.31 g) as a solid: 1H NMR (CDCl3) delta 1.44 (9H), 2.35 (1H), 2.70 (3H), 3.13 (2H), 3.33 (1H), 3.77 (3H), 4.22 (1H), 5.00 (1H), 6.48 (1H), 7.18 (2H), 7.31 (3H), 7.44 (1H), 7.56 (2H); 13C NMR (CDCl3) delta 171.6, 168.9, 162.5, 136.5, 135.9, 132.4, 131.0, 130.2, 128.2, 120.5, 81.7, 77.3, 53.3, 52.6, 37.0, 28.2, 26.5; IR (mull) 3296, 2924, 1744, 1685, 1668, 1605, 1536, 1515, 1432, 1412, 1321, 1294, 1260, 1244, 1213, 1195, 1161, 798 cm-1; MS (FAB) m/z (rel. intensity) 598 (M+H, 3), 596 (M+H, 5), Anal. Calcd for C27H31Cl2N3O6S: C, 54.36; H, 5.24; N, 7.04. Found: C, 54.23; H, 5.24; N, 6.86. Corrected for 0.60% H2O, found by Karl Fischer analysis.
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Reference£º
Patent; Pharmacia & Upjohn Company; Tanabe Seiyaku Co., Ltd.; US6685617; (2004); B1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem