Methanesulfonamide → (1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-(4-(methylsulfonylcarbamoyl)phenyl)-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]chrysene-3a-carboxylic acid

HRID 406884Notes

Reaction equation

HRID 406884 reaction equation
Cl[C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([CH3:48])([CH3:47])[C@H:12]3[C@:25]([CH3:28])([CH2:26][CH:27]=2)[CH:24]2[C@:15]([CH3:46])([C@@:16]4([CH3:45])[C@H:21]([CH2:22][CH2:23]2)[C@H:20]2[C@H:29]([C:32]([CH3:34])=[CH2:33])[CH2:30][CH2:31][C@:19]2([C:35]([O:37]CC2C=CC=CC=2)=[O:36])[CH2:18][CH2:17]4)[CH2:14][CH2:13]3)=[CH:6][CH:5]=1)=[O:3].[CH3:49][S:50]([NH2:53])(=[O:52])=[O:51]>>[CH3:45][C@:16]12[C@@:15]3([CH3:46])[CH:24]([C@:25]4([CH3:28])[C@@H:12]([CH2:13][CH2:14]3)[C:11]([CH3:47])([CH3:48])[C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:2](=[O:3])[NH:53][S:50]([CH3:49])(=[O:52])=[O:51])=[CH:5][CH:6]=3)=[CH:27][CH2:26]4)[CH2:23][CH2:22][C@@H:21]1[C@H:20]1[C@H:29]([C:32]([CH3:34])=[CH2:33])[CH2:30][CH2:31][C@:19]1([C:35]([OH:37])=[O:36])[CH2:18][CH2:17]2

Participants

3

Reactant 2

HCID 72879MethanesulfonamideHCID 86666259(1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-benzyl 9-(4-(chlorocarbonyl)phenyl)-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]chrysene-3a-carboxylate

Product 1

HCID 67776353(1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-9-(4-(methylsulfonylcarbamoyl)phenyl)-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]chrysene-3a-carboxylic acid

Procedure

The title compound was prepared from the procedure described above for (1R,3aS,5aR,5bR,7aR,11aS,13aR,13bR)-benzyl 9-(4-(chlorocarbonyl)phenyl)-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]chrysene-3a-carboxylate using methanesulfonamide as the reactant sulfonamide. The title compound was isolated as a white solid (3.2 mg, 7%). LCMS: m/e 636.51 (M+H)+, 2.13 min (method 7). 1H NMR (500 MHz, DMSO-D6) δ ppm 0.88 (d, J=3.05 Hz, 6H), 0.94 (s, 6H), 0.98 (s, 3H), 1.11-1.62 (m, 15H), 1.63-1.72 (m, 5H), 1.77-1.88 (m, 2H), 2.03-2.17 (m, 2H), 2.24-2.35 (m, 1H), 2.97 (d, J=4.58 Hz, 1H), 3.57 (s, 3H), 4.58 (s, 1H), 4.71 (d, J=1.83 Hz, 1H), 5.23 (d, J=4.58 Hz, 1H), 7.17 (d, J=8.24 Hz, 2H), 7.86 (d, J=8.24 Hz, 2H), 12.03 (s, 1H), 12.10 (br. s., 1H).

Workup

  1. customThe title compound was prepared from the procedure

Sources & evidence

ORD record
ord-e7760843df42462cb20a1e8399fa1919
Source dataset
uspto-grants-2014_06
Patent number
US08754068B2

Reaction notes

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