(1R,5S)-8-oxa-3-azabicyclo[3.2.1]octane → 4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-3a-[2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)ethylamino]-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid

HRID 338652Notes

Reaction equation

HRID 338652 reaction equation
[C@@H]12N([CH2:10][CH2:11][NH:12][C@:13]34[CH2:47][CH2:46][C@@H:45]([C:48]([CH3:50])=[CH2:49])[C@@H:14]3[C@@H:15]3[C@@:28]([CH3:31])([CH2:29][CH2:30]4)[C@@:27]4([CH3:32])[C@@H:18]([C@:19]5([CH3:44])[C@@H:24]([CH2:25][CH2:26]4)[C:23]([CH3:34])([CH3:33])[C:22]([C:35]4[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=4)=[CH:21][CH2:20]5)[CH2:17][CH2:16]3)[C@@H](CCC1)COC2.[C@@H:51]12[O:58][C@@H:55]([CH2:56][CH2:57]1)[CH2:54][NH:53][CH2:52]2>>[CH:55]12[O:58][CH:51]([CH2:57][CH2:56]1)[CH2:52][N:53]([CH2:10][CH2:11][NH:12][C@:13]13[CH2:47][CH2:46][C@@H:45]([C:48]([CH3:50])=[CH2:49])[C@@H:14]1[C@@H:15]1[C@@:28]([CH3:31])([CH2:29][CH2:30]3)[C@@:27]3([CH3:32])[C@@H:18]([C@:19]4([CH3:44])[C@@H:24]([CH2:25][CH2:26]3)[C:23]([CH3:33])([CH3:34])[C:22]([C:35]3[CH:43]=[CH:42][C:38]([C:39]([OH:41])=[O:40])=[CH:37][CH:36]=3)=[CH:21][CH2:20]4)[CH2:17][CH2:16]1)[CH2:54]2

Participants

3

Reactant 2

HCID 46831336(1R,5S)-8-oxa-3-azabicyclo[3.2.1]octaneHCID 867018124-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((1R,5S)-3-oxa-9-azabicyclo[3.3.1]nonan-9-yl)ethyl)amino)-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 865764874-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-3a-[2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)ethylamino]-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[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-((1R,5S)-3-oxa-9-azabicyclo[3.3.1]nonan-9-yl)ethyl)amino)-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 (1R,5S)-8-oxa-3-azabicyclo[3.2.1]octane as the alkylating amine in step 3. The product was isolated as a white solid (8 mg, 28%). LCMS: m/e 669.7 (M+H)+, 2.11 min (method 4). 1H NMR (500 MHz, ACETONITRILE-d3) δ 8.17-7.83 (m, 2H), 7.43-7.12 (m, 2H), 5.32 (dd, J=6.2, 1.8 Hz, 1H), 4.80 (d, J=1.7 Hz, 1H), 4.72 (d, J=1.4 Hz, 1H), 4.37 (br. s., 2H), 3.14 (br. s., 4H), 2.99 (br. s., 4H), 2.92-2.81 (m, 1H), 2.68-2.44 (m, 2H), 2.27-1.15 (m, 24H), 1.75 (s, 3H), 1.21 (s, 3H), 1.09 (s, 3H), 1.05 (s, 3H), 0.98 (s, 3H), 0.96 (s, 3H).

Sources & evidence

ORD record
ord-d4830cf5fe77452094d74d9635529903
Source dataset
uspto-grants-2014_11
Patent number
US08889854B2

Reaction notes

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