4-(3-Aminopropyl)-1lambda~6~,4-thiazinane-1,1-dione → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(((3-(1,1-dioxido-4-thiomorpholinyl)propyl)amino)methyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)-2-fluorobenzoic acid

HRID 405083Notes

Reaction equation

HRID 405083 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([C:12]2[C:13]([CH3:42])([CH3:41])[C@H:14]3[C@:27]([CH3:30])([CH2:28][CH:29]=2)[C@@H:26]2[C@:17]([CH3:40])([C@@:18]4([CH3:39])[C@H:23]([CH2:24][CH2:25]2)[C@H:22]2[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:21]2([CH:37]=O)[CH2:20][CH2:19]4)[CH2:16][CH2:15]3)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=[O:5].[NH2:43][CH2:44][CH2:45][CH2:46][N:47]1[CH2:52][CH2:51][S:50](=[O:54])(=[O:53])[CH2:49][CH2:48]1>>[O:53]=[S:50]1(=[O:54])[CH2:49][CH2:48][N:47]([CH2:46][CH2:45][CH2:44][NH:43][CH2:37][C@:21]23[CH2:33][CH2:32][C@@H:31]([C:34]([CH3:36])=[CH2:35])[C@@H:22]2[C@@H:23]2[C@@:18]([CH3:39])([CH2:19][CH2:20]3)[C@@:17]3([CH3:40])[C@@H:26]([C@:27]4([CH3:30])[C@@H:14]([CH2:15][CH2:16]3)[C:13]([CH3:41])([CH3:42])[C:12]([C:10]3[CH:9]=[CH:8][C:3]([C:4]([OH:6])=[O:5])=[C:2]([F:1])[CH:11]=3)=[CH:29][CH2:28]4)[CH2:25][CH2:24]2)[CH2:52][CH2:51]1

Participants

3

Reactant 2

HCID 247280544-(3-Aminopropyl)-1lambda~6~,4-thiazinane-1,1-dioneHCID 86676413methyl 2-fluoro-4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-formyl-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

Product 1

HCID 601524964-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(((3-(1,1-dioxido-4-thiomorpholinyl)propyl)amino)methyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)-2-fluorobenzoic acid

Procedure

The title compound was prepared following steps 5 and 6 using methyl 2-fluoro-4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-formyl-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate and 4-(3-aminopropyl) thiomorpholine 1,1-dioxide as the reactant amine. The product was isolated as a white solid (50 mg, 55.0%). LCMS: m/e 737.5 (MH+), 2.53 min (method 3). 1H NMR (400 MHz, MeOD) δ ppm 7.85 (d, J=3.8 Hz, 1H), 7.01-7.14 (m, 1H), 6.98 (br. s., 1H), 5.37 (br. s., 1H), 4.78 (br. s., 1H), 4.67 (br. s., 1H), 3.56 (br. s., 4H), 3.43 (br. s., 4H), 3.21 (m, 3H), 3.12 (br. s., 2H), 2.90 (br. s., 1H), 2.53 (br. s., 1H), 2.16 (br. s., 4H), 1.75 (br. s., 10H), 1.53 (br. s., 8H), 1.31 (br. s., 3H), 1.19 (br. s., 5H), 1.10 (br. s., 3H), 1.05 (br. s., 3H), 0.99 (d, J=8.5 Hz, 6H). 19F NMR (376 MHz, MeOD) δ ppm −112.6 (s, 1 F).

Sources & evidence

ORD record
ord-8cdd84ca14b446b1bfc52a00bb6099c9
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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