Isobutyric Acid → HCID 86676661, compound

HRID 85761Notes

Reaction equation

[CH3:1][C@:2]12[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:33])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:22])([CH3:21])[C:14]([C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[CH:25][CH:24]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8][C@@H:7]1[C@H:6]1[C@H:34]([C:37]([CH3:39])=[CH2:38])[CH2:35][CH2:36][C@:5]1([NH:40][CH2:41][CH2:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1)[CH2:4][CH2:3]2.[C:49](O)(=[O:53])[CH:50]([CH3:52])[CH3:51]>>[C:49]([N:46]1[CH2:47][CH2:48][N:43]([CH2:42][CH2:41][NH:40][C@:5]23[CH2:36][CH2:35][C@@H:34]([C:37]([CH3:39])=[CH2:38])[C@@H:6]2[C@@H:7]2[C@@:2]([CH3:1])([CH2:3][CH2:4]3)[C@@:19]3([CH3:20])[C@@H:10]([C@:11]4([CH3:33])[C@@H:16]([CH2:17][CH2:18]3)[C:15]([CH3:22])([CH3:21])[C:14]([C:23]3[CH:24]=[CH:25][C:26]([C:27]([OH:29])=[O:28])=[CH:31][CH:32]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8]2)[CH2:44][CH2:45]1)(=[O:53])[CH:50]([CH3:52])[CH3:51]

Participants

Reactant 2

HCID 6590Isobutyric Acid

HCID 86676640methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(piperazin-1-yl)ethyl)amino)-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 86676661HCID 86676661, compound

Procedure

The title compound (0.4 mg) was prepared from methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(piperazin-1-yl)ethyl)amino)-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 following the general procedure as described above using isobutyric acid as the acylating agent. LCMS: m/e 712.8 (M+H)+, 4.46 min (method 15). 1H NMR (500 MHz, METHANOL-d4) δ 7.88 (d, J=8.2 Hz, 2H), 7.15 (d, J=7.9 Hz, 2H), 5.30 (d, J=4.9 Hz, 1H), 4.78 (s, 1H), 4.67 (s, 1H), 3.77-3.54 (m, 4H), 2.97 (dt, J=13.4, 6.6 Hz, 2H), 2.86-2.71 (m, 3H), 2.70-2.51 (m, 4H), 2.46 (br. s., 1H), 2.15 (dd, J=17.1, 6.4 Hz, 1H), 2.08-1.82 (m, 5H), 1.75 (s, 3H), 1.73-1.18 (m, 16H), 1.22 (s, 3H), 1.11 (d, J=6.7 Hz, 6H), 1.10 (s, 3H), 1.05 (s, 3H), 0.97 (s., 3H), 0.97 (s., 3H),

Workup

customm/e 712.8 (M+H)+, 4.46 min (method 15)

Sources & evidence

ORD record: ord-9c7869850d9f43d9914f974c8487843e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846647B2

Reaction notes

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