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)-3-fluorobenzoic acid

HRID 405082Notes

Reaction equation

HRID 405082 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]1[C:13]([CH3:42])([CH3:41])[C@H:14]2[C@:27]([CH3:30])([CH2:28][CH:29]=1)[C@@H:26]1[C@:17]([CH3:40])([C@@:18]3([CH3:39])[C@H:23]([CH2:24][CH2:25]1)[C@H:22]1[C@H:31]([C:34]([CH3:36])=[CH2:35])[CH2:32][CH2:33][C@:21]1([CH:37]=O)[CH2:20][CH2:19]3)[CH2:16][CH2:15]2)[C:5]([O:7]C)=[O:6].[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:11]3[CH:10]=[CH:9][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=3[F:1])=[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 86676412methyl 3-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 715981924-((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)-3-fluorobenzoic acid

Procedure

The title compound was prepared following steps 5 and 6 using methyl 3-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 (70 mg, 68.0%). LCMS: m/e 737.5 (MH+), 2.59 min (method 3). 1H NMR (400 MHz, MeOD) δ ppm 7.77 (d, J=7.8 Hz, 1H), 7.67 (d, J=9.8 Hz, 1H), 7.19-7.31 (m, 1H), 5.38 (d, J=4.8 Hz, 1H), 4.78 (br. s., 1H), 4.67 (br. s., 1H), 3.41 (br. s., 4H), 3.30-3.38 (m, 4H), 3.27 (d, J=12.5 Hz, 1H), 3.21 (br. s., 2H), 3.00 (t, J=6.4 Hz, 2H), 2.90 (br. s., 1H), 2.53 (br. s., 1H), 2.10 (br. s., 4H), 1.84 (br. s., 3H), 1.75 (br. s., 7H), 1.54 (br. s., 8H), 1.36 (br. s., 3H), 1.20 (br. s., 5H), 1.11 (br. s., 3H), 1.07 (br. s., 3H), 0.98 (br. s., 3H), 0.94 (br. s., 3H). 19F NMR (376 MHz, MeOD) δ ppm −113.31 (s, 1 F).

Sources & evidence

ORD record
ord-b172c3cebee941e78f05906337499735
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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