Methyl vinyl sulfone → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(2-(methylsulfonyl)ethylamino)-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)benzoic acid

HRID 85616Notes

Reaction equation

HRID 85616 reaction equation
OC[CH2:3][S:4]([CH2:7][CH2:8][NH:9][C@:10]12[CH2:44][CH2:43][C@@H:42]([C:45]([CH3:47])=[CH2:46])[C@@H:11]1[C@@H:12]1[C@@:25]([CH3:28])([CH2:26][CH2:27]2)[C@@:24]2([CH3:29])[C@@H:15]([C@:16]3([CH3:41])[C@@H:21]([CH2:22][CH2:23]2)[C:20]([CH3:31])([CH3:30])[C:19]([C:32]2[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=2)=[CH:18][CH2:17]3)[CH2:14][CH2:13]1)(=[O:6])=[O:5].CS(C=C)(=O)=O>>[CH3:28][C@:25]12[C@@:24]3([CH3:29])[C@@H:15]([C@:16]4([CH3:41])[C@@H:21]([CH2:22][CH2:23]3)[C:20]([CH3:30])([CH3:31])[C:19]([C:32]3[CH:33]=[CH:34][C:35]([C:36]([OH:38])=[O:37])=[CH:39][CH:40]=3)=[CH:18][CH2:17]4)[CH2:14][CH2:13][C@@H:12]1[C@H:11]1[C@H:42]([C:45]([CH3:47])=[CH2:46])[CH2:43][CH2:44][C@:10]1([NH:9][CH2:8][CH2:7][S:4]([CH3:3])(=[O:6])=[O:5])[CH2:27][CH2:26]2

Participants

3

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 683579204-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(2-hydroxyethylsulfonyl)ethylamino)-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)benzoic acid

Product 1

HCID 683580494-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-(2-(methylsulfonyl)ethylamino)-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)benzoic acid

Procedure

The title compound was prepared following the method described above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-(2-hydroxyethylsulfonyl)ethylamino)-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)benzoic acid using methylsulfonylethene instead of vinylsulfonylethene in Step 1. The product was isolated as a white solid (6 mg, 39%). LCMS: m/e 636.37 (M+H)+, 2.53 min (method 10). 1H NMR (500 MHz, Acetic acid d4) δ ppm 8.04 (d, J=8.24 Hz, 2H), 7.30 (d, J=8.24 Hz, 2H), 5.44-5.33 (m, 1H), 4.88 (s, 1H), 4.76 (s, 1H), 4.17-4.00 (m, 1H), 3.93-3.69 (m, 3H), 3.22 (s, 3H), 3.00-2.85 (m, 1H), 2.40-1.26 (m, 22H), 1.77 (s, 3H), 1.23 (s, 3H), 1.14 (s, 3H), 1.10 (s, 3H), 1.02 (s, 3H), 1.00 (s, 3H).

Sources & evidence

ORD record
ord-4da613de18954019a0d25fe9def006b9
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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