oxo(piperidin-1-yl)acetic acid → HCID 86676648, compound

HRID 85748Notes

Reaction equation

[CH3:1][N:2]([CH3:54])[C:3](=[O:53])[C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][NH:14][C@:15]23[CH2:49][CH2:48][C@@H:47]([C:50]([CH3:52])=[CH2:51])[C@@H:16]2[C@@H:17]2[C@@:30]([CH3:33])([CH2:31][CH2:32]3)[C@@:29]3([CH3:34])[C@@H:20]([C@:21]4([CH3:46])[C@@H:26]([CH2:27][CH2:28]3)[C:25]([CH3:36])([CH3:35])[C:24]([C:37]3[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=3)=[CH:23][CH2:22]4)[CH2:19][CH2:18]2)[CH2:8][CH2:7]1)=[O:5].O=C(N1CC[CH2:63][CH2:62][CH2:61]1)C(O)=O>>[CH3:33][C@:30]12[C@@:29]3([CH3:34])[C@@H:20]([C@:21]4([CH3:46])[C@@H:26]([CH2:27][CH2:28]3)[C:25]([CH3:36])([CH3:35])[C:24]([C:37]3[CH:38]=[CH:39][C:40]([C:41]([OH:43])=[O:42])=[CH:44][CH:45]=3)=[CH:23][CH2:22]4)[CH2:19][CH2:18][C@@H:17]1[C@H:16]1[C@H:47]([C:50]([CH3:52])=[CH2:51])[CH2:48][CH2:49][C@:15]1([NH:14][CH2:13][CH2:12][N:9]1[CH2:10][CH2:11][N:6]([C:4](=[O:5])[C:3](=[O:53])[N:2]3[CH2:1][CH2:63][CH2:62][CH2:61][CH2:54]3)[CH2:7][CH2:8]1)[CH2:32][CH2:31]2

Participants

Reactant 2

HCID 7174533oxo(piperidin-1-yl)acetic acid

HCID 866766454-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(4-(2-(dimethylamino)-2-oxoacetyl)piperazin-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

Product 1

HCID 86676648HCID 86676648, compound

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-(4-(2-(dimethylamino)-2-oxoacetyl)piperazin-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 using 2-oxo-2-(piperidin-1-yl)acetic acid as the acid in Step 1. The product was isolated as a white solid (1.1 mg, 18%). LCMS: m/e 781.7 (M+H)+, 1.72 min (method 11). 1H NMR (500 MHz, CHLOROFORM-d) δ 7.99 (d, J=8.4 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 5.31 (d, J=4.6 Hz, 1H), 4.77 (s, 1H), 4.65 (s, 1H), 3.84 (dd, J=7.6, 2.7 Hz, 1H), 3.68-3.56 (m, 3H), 3.49 (t, J=4.9 Hz, 2H), 3.43-3.30 (m, 2H), 2.93-2.63 (m, 9H), 2.60-1.05 (m, 28H), 1.72 (s, 3H), 1.17 (s, 3H), 1.04 (s, 3H), 1.00 (s, 3H), 0.97 (s, 3H), 0.97 (s, 3H).

Sources & evidence

ORD record: ord-667929936fdc43448bb4003d8c386b08
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846647B2

Reaction notes

Loading…