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 → 4-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3a-((2-(methylamino)-2-oxoethyl)amino)icosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

HRID 85716

反応式

HRID 85716 の反応式
O=S1(=O)CCC(NCCN[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(O)=O)=CC=3)=CC4)CC2)C1.[CH3:50][C@:51]12[C@@:68]3([CH3:69])[C@@H:59]([C@:60]4([CH3:81])[C@@H:65]([CH2:66][CH2:67]3)[C:64]([CH3:71])([CH3:70])[C:63]([C:72]3[CH:80]=[CH:79][C:75]([C:76]([OH:78])=[O:77])=[CH:74][CH:73]=3)=[CH:62][CH2:61]4)[CH2:58][CH2:57][C@@H:56]1[C@H:55]1[C@H:82]([C:85]([CH3:87])=[CH2:86])[CH2:83][CH2:84][C@:54]1([NH:88][CH2:89][C:90]([NH:92][CH3:93])=[O:91])[CH2:53][CH2:52]2>>[CH:85]([C@H:82]1[C@@H:55]2[C@@H:56]3[C@@:51]([CH3:50])([CH2:52][CH2:53][C@@:54]2([NH:88][CH2:89][C:90]([NH:92][CH3:93])=[O:91])[CH2:84][CH2:83]1)[C@@:68]1([CH3:69])[C@@H:59]([C@:60]2([CH3:81])[C@@H:65]([CH2:66][CH2:67]1)[C:64]([CH3:71])([CH3:70])[C@@H:63]([C:72]1[CH:80]=[CH:79][C:75]([C:76]([OH:78])=[O:77])=[CH:74][CH:73]=1)[CH2:62][CH2:61]2)[CH2:58][CH2:57]3)([CH3:87])[CH3:86]

参加物

3

反応物 2

HCID 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 acidHCID 866765974-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(methylamino)-2-oxoethyl)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)benzoic acid

生成物 1

HCID 683581614-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-3a-((2-(methylamino)-2-oxoethyl)amino)icosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid

実験手順

The title compound was prepared following the method described above for the synthesis 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 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(methylamino)-2-oxoethyl)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)benzoic acid as the starting material. The product was isolated as a white solid (3 mg, 28%). LCMS: m/e 605.45 (M+H)+, 2.58 min (method 10). 1H NMR (500 MHz, Acetic) δ 8.02 (d, J=8.2 Hz, 2H), 7.36 (d, J=8.2 Hz, 2H), 4.22 (d, J=15.6 Hz, 1H), 3.85 (d, J=15.6 Hz, 1H), 2.87 (s, 3H), 2.50 (dd, J=13.1, 2.4 Hz, 1H), 2.35-1.02 (m, 26H), 1.28 (s, 3H), 1.13 (s, 3H), 1.08 (s, 3H), 0.95 (d, J=6.7 Hz, 3H), 0.87 (d, J=6.7 Hz, 3H), 0.84 (s, 3H), 0.80 (s, 3H).

出典と根拠

ORDレコード
ord-7b939239d65c40d6a3e35c2b3a526263
出典データセット
uspto-grants-2014_09
特許番号
US08846647B2

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