Butyric Acid → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(4-butyrylpiperazin-1-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

HRID 85758Notes

Reaction equation

HRID 85758 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]3C=CC(C(OC)=O)=[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]([OH:54])(=[O:53])[CH2:50][CH2:51][CH3:52]>>[C:49]([N:46]1[CH2:45][CH2:44][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:50]([C:49]([OH:54])=[O:53])=[CH:51][CH:52]=3)=[CH:13][CH2:12]4)[CH2:9][CH2:8]2)[CH2:48][CH2:47]1)(=[O:53])[CH2:50][CH2:51][CH3:52]

Participants

3

Reactant 2

HCID 264Butyric AcidHCID 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 866766584-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(4-butyrylpiperazin-1-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

Procedure

The title compound (1.2 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 butyric acid as the acylating agent. LCMS: m/e 712.8 (M+H)+, 4.97 min (method 15). 1H NMR (500 MHz, METHANOL-d4) δ 7.89 (d, J=8.2 Hz, 2H), 7.16 (d, J=8.2 Hz, 2H), 5.30 (d, J=4.6 Hz, 1H), 4.78 (s, 1H), 4.68 (s, 1H), 3.79-3.55 (m, 4H), 3.12-2.98 (m, 1H), 2.97-2.82 (m, 2H), 2.78 (td, J=10.9, 5.0 Hz, 1H), 2.71-2.61 (m, 3H), 2.60-2.54 (m, 1H), 2.52-2.44 (m, 1H), 2.40 (t, J=7.5 Hz, 2H), 2.19-1.80 (m, 6H), 1.75 (s, 3H), 1.73-1.04 (m, 18H), 1.23 (s, 3H), 1.11 (s, 3H), 1.05 (s, 3H), 0.99 (t, J=7.5 Hz, 3H), 0.97 (s, 3H), 0.97 (s, 3H).

Workup

  1. customm/e 712.8 (M+H)+, 4.97 min (method 15)

Sources & evidence

ORD record
ord-f5a4e5d72a86496faee298f8ce5b3cc9
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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