4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-3a-[[2-(4-methylsulfonylpiperazin-1-yl)ethylamino]methyl]-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid → 4-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-1-isopropenyl-3a-[(2-methoxyethylamino)methyl]-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid

HRID 405105Notes

Reaction equation

HRID 405105 reaction equation
N1(C[C@]23CC[C@@H](C(C)=C)[C@@H]2[C@@H]2[C@@](C)(CC3)[C@@]3(C)[C@@H]([C@]4(C)[C@@H](CC3)C(C)(C)C(C3C=CC([C:31](OC(C)(C)C)=[O:32])=CC=3)=CC4)CC2)CC1.[CH3:47][C@:48]12[C@@:65]3([CH3:66])[C@@H:56]([C@:57]4([CH3:78])[C@@H:62]([CH2:63][CH2:64]3)[C:61]([CH3:68])([CH3:67])[C:60]([C:69]3[CH:77]=[CH:76][C:72]([C:73]([OH:75])=[O:74])=[CH:71][CH:70]=3)=[CH:59][CH2:58]4)[CH2:55][CH2:54][C@@H:53]1[C@H:52]1[C@H:79]([C:82]([CH3:84])=[CH2:83])[CH2:80][CH2:81][C@:51]1([CH2:85][NH:86][CH2:87][CH2:88]N1CCN(S(C)(=O)=O)CC1)[CH2:50][CH2:49]2>CO>[CH3:31][O:32][CH2:88][CH2:87][NH:86][CH2:85][C@:51]12[CH2:81][CH2:80][C@@H:79]([C:82]([CH3:84])=[CH2:83])[C@@H:52]1[C@@H:53]1[C@@:48]([CH3:47])([CH2:49][CH2:50]2)[C@@:65]2([CH3:66])[C@@H:56]([C@:57]3([CH3:78])[C@@H:62]([CH2:63][CH2:64]2)[C:61]([CH3:67])([CH3:68])[C:60]([C:69]2[CH:77]=[CH:76][C:72]([C:73]([OH:75])=[O:74])=[CH:71][CH:70]=2)=[CH:59][CH2:58]3)[CH2:55][CH2:54]1

Participants

4

Reactant 2

HCID 715976824-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-3a-[[2-(4-methylsulfonylpiperazin-1-yl)ethylamino]methyl]-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acidHCID 86676422tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aziridin-1-ylmethyl)-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)benzoate

Product 1

HCID 715972534-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-1-isopropenyl-3a-[(2-methoxyethylamino)methyl]-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared from tert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aziridin-1-ylmethyl)-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)benzoate following the procedure described above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperazin-1-yl)ethylamino)methyl)-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 methanol as reagent in step 1. The product was isolated as a white solid (1.6 mg, 5.2%). LCMS: m/e 602.49 (MH+), 2.40 min (method 9). 1H NMR (500 MHz, METHANOL-d4) δ 7.85 (d, J=7.6 Hz, 2H), 7.12 (d, J=7.6 Hz, 2H), 5.29 (s, 1H), 4.79-4.76 (s, 1H), 4.66 (s, 1H), 3.67-3.64 (m, 2H), 3.43 (s, 3H), 3.21-3.15 (m, 3H), 2.69-2.62 (m, 1H), 2.52 (m, 1H), 2.19-2.10 (m, 1H), 2.07-2.00 (m, 1H), 1.79 (m, 8H), 1.57 (m, 8H), 1.40-1.24 (m, 7H), 1.18 (m, 4H), 1.09 (3H, s), 1.05 (3H, s), 0.97 (3H, s), 0.96 (3H, s).

Sources & evidence

ORD record
ord-f89cfe3c4f024ada81120ebd75e6444a
Source dataset
uspto-grants-2014_06
Patent number
US08748415B2

Reaction notes

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