6-(2-Chloroethyl)-2-oxa-6-azaspiro[3.3]heptane → 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(2-oxa-6-azaspiro[3.3]heptan-6-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 85728Notes

Reaction equation

HRID 85728 reaction equation
O=S1(=O)CCC(NCC[NH:10][C@:11]23[CH2:45][CH2:44][C@@H:43]([C:46]([CH3:48])=[CH2:47])[C@@H:12]2[C@@H:13]2[C@@:26]([CH3:29])([CH2:27][CH2:28]3)[C@@:25]3([CH3:30])[C@@H:16]([C@:17]4([CH3:42])[C@@H:22]([CH2:23][CH2:24]3)[C:21]([CH3:32])([CH3:31])[C:20]([C:33]3[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[CH:35][CH:34]=3)=[CH:19][CH2:18]4)[CH2:15][CH2:14]2)C1.Cl[CH2:51][CH2:52][N:53]1[CH2:59][C:55]2([CH2:58][O:57][CH2:56]2)[CH2:54]1>>[CH2:58]1[C:55]2([CH2:59][N:53]([CH2:52][CH2:51][NH:10][C@:11]34[CH2:45][CH2:44][C@@H:43]([C:46]([CH3:48])=[CH2:47])[C@@H:12]3[C@@H:13]3[C@@:26]([CH3:29])([CH2:27][CH2:28]4)[C@@:25]4([CH3:30])[C@@H:16]([C@:17]5([CH3:42])[C@@H:22]([CH2:23][CH2:24]4)[C:21]([CH3:32])([CH3:31])[C:20]([C:33]4[CH:34]=[CH:35][C:36]([C:37]([OH:39])=[O:38])=[CH:40][CH:41]=4)=[CH:19][CH2:18]5)[CH2:15][CH2:14]3)[CH2:54]2)[CH2:56][O:57]1

Participants

3

Reactant 2

HCID 682759396-(2-Chloroethyl)-2-oxa-6-azaspiro[3.3]heptaneHCID 683581604-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((1,1-dioxidotetrahydrothiophen-3-yl)amino)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 601524994-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(2-oxa-6-azaspiro[3.3]heptan-6-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 was prepared following the method described above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-((1,1-dioxidotetrahydrothiophen-3-yl)amino)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 6-(2-chloroethyl)-2-oxa-6-azaspiro[3.3]heptane (prepared as described below) as the alkylating reagent in Step 3. The product was isolated as a white solid (1.1 mg, 18%). LCMS: m/e 655.53 (M+H)+, 2.29 min (method 11). 1H NMR (500 MHz, Acetic) δ 8.04 (d, J=8.2 Hz, 2H), 7.30 (d, J=8.5 Hz, 2H), 5.37 (d, J=4.9 Hz, 1H), 4.93 (s., 4H), 4.86 (s, 1H), 4.75 (br. s., 1H), 4.71-4.32 (m, 4H), 4.05-3.86 (m, 2H), 3.70-3.40 (m, 2H), 3.00-2.66 (m, 1H), 2.25-1.05 (m, 22H), 1.76 (s, 3H), 1.18 (s, 3H), 1.13 (s, 3H), 1.08 (s, 3H), 1.02 (s, 3H), 1.00 (s, 3H).

Sources & evidence

ORD record
ord-391bddb5c2434073bc29016c4ba3b3b9
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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