4-Fluorobenzenesulfonamide

31. N-(4-fluorophenyl)sulfonyl-a-dehydrocyclohexylglycine.; 2-cyclohexyl-2-oxoethanoic acid (3.0 g, 19.2 mmol) was combined with p-toluenesulfonamide (2.70 g, 15.4 mmol) in toluene (21 mL) and diethyleneglycol diethyl ether (3 mL). MSA (0.10 mL, 1.5 mmol) was added, and this mixture was heated at reflux for 28h, then cooled to rt. The resulting solids were mixed with EtOAc (35 mL) and NaHC03 (2.6 g) in water (60 mL), until all materials dissolved. The aqueous was separated, and the organics were washed with NaH C03 (0.40 g) in water (10 mL). The combined aqueous layer was then washed with EtOAc (20 mL). The aqueous layer was cooled to 0 C, then treated with HCl (12.1 N, 3.1 mL). The resulting solids were filtered and washed with water and dried to give 3.0 g of crude material. The solids were then recrystallized from toluene/ methanol to give 2.8 g of white solid (58% yield). mp 214-215 C. ¹H-NMR (400 MHz, CD30D) d 7.83-7.88 (m, 2H), 7.23-7.29 (m, 2H), 2.61-2.65 (m, 2H), 2.21-2.24 (m, 2H), 1.55-1.59 (m, 4H), 1.41-1.46 (m, 2H); ¹3C NMR (100 MHz, CD30D) 167.2, 166.3, 163.7, 155.3, 136.5 (2 peaks), 129.9 (2 peaks), 118.3, 115.5, 115.3, 31.0, 30.5, 27.6, 27.2, 25.7 ppm. HRMS calcd for C14H15FN04S (M-H) : 312.0706, Found: 312.0707.Example 10 27. N-(4-fluorobenzene)sulfonyl-alpha-dehydrovaline.; 3-methyl-2-oxobutyic acid, sodium salt (5.0 g, 36.2 mmol) was slurried in MTBE (25 mL) and cooled to 0 C, then HCI (12.1 N, 3.1 mL) was added. The resulting biphasic was warmed to rt, then saturated with Na2S04. The inorganic solids were filtered and washed with MTBE (25 mL). The combined organics were stripped to give a light-yellow oil. This oil was dissolved in toluene (35 mL) and diethyleneglycol diethyl ether (5 mL) and p-toluenesulfonamide (5.1 g, 29.0 mmol) then methanesulfonic acid (0.19 mL, 2.9 mmol) were added. The resulting mixture was heated at reflux with Dean-Stark removal of water for 24h, then cooled to 5 C. The resulting solid was filtered, and dried to give 5.4 g of crude material, which was recrystallized from MeOH/ water (16 mL/ 38 mL) to give 4.90 g of pure white solid (62% isolated yield). mp 172-173 C. IH-NMR (400 MHz, CD30D) d 7.83-7.86 (m, 2H), 7.22-7.27 (m, 2H), 2.12 (s, 3H), 1.87 (s, 3H); ¹3C NMR (100 MHz, CD30D) 166.6, 166.3, 163.7, 151.6, 136.7 (2 peaks), 129.9, 129.8, 120.8, 115.5, 115.3, 22.0, 20.4 ppm. HRMS calcd for C11H11FNO4S (M-H) : 272.0393, Found: 272.0398.[859] To a mixture of

Pharmaceutical intermediates

Molecular Weight:175.18
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:175.01032777
Monoisotopic Mass:175.01032777
Topological Polar Surface Area:68.5
Heavy Atom Count:11
Complexity:213
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes