HCID 78320689, compound → HCID 86731502, compound

HRID 1773044Notes

Reaction equation

FC1(C(O)=O)CCC(=CC2C(C)(C)[C@H]3[C@](C)(CC=2)[C@@H]2[C@](C)([C@@]4(C)[C@H](CC2)[C@H]2[C@H](C(C)=C)CC[C@]2(NCCN2CCC(S(C)(=O)=O)CC2)CC4)CC3)CC1.[O:54]=[S:55]1(=[O:101])[CH2:60][CH2:59][N:58]([CH2:61][CH2:62][NH:63][C@:64]23[CH2:97][CH2:96][C@@H:95]([C:98]([CH3:100])=[CH2:99])[C@@H:65]2[C@@H:66]2[C@@:79]([CH3:82])([CH2:80][CH2:81]3)[C@@:78]3([CH3:83])[C@@H:69]([C@:70]4([CH3:94])[C@@H:75]([CH2:76][CH2:77]3)[C:74]([CH3:85])([CH3:84])[C:73]([CH:86]=[CH:87][CH:88]=[CH:89][C:90]([O:92]C)=[O:91])=[CH:72][CH2:71]4)[CH2:68][CH2:67]2)[CH2:57][CH2:56]1>>[O:101]=[S:55]1(=[O:54])[CH2:60][CH2:59][N:58]([CH2:61][CH2:62][NH:63][C@:64]23[CH2:97][CH2:96][C@@H:95]([C:98]([CH3:100])=[CH2:99])[C@@H:65]2[C@@H:66]2[C@@:79]([CH3:82])([CH2:80][CH2:81]3)[C@@:78]3([CH3:83])[C@@H:69]([C@:70]4([CH3:94])[C@@H:75]([CH2:76][CH2:77]3)[C:74]([CH3:84])([CH3:85])[C:73]([CH:86]=[CH:87][CH:88]=[CH:89][C:90]([OH:92])=[O:91])=[CH:72][CH2:71]4)[CH2:68][CH2:67]2)[CH2:57][CH2:56]1

Participants

Reactant 2

HCID 78320689HCID 78320689, compound

HCID 86731503HCID 86731503, compound

Product 1

HCID 86731502HCID 86731502, compound

Procedure

5-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)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)penta-2,4-dienoic acid was prepared following the procedure described in step 2 of the preparation of 1-fluoro-4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-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)methylene)cyclohexanecarboxylic acid using the corresponding crude product from step 1 as the reactant. The title compound was obtained as a mixture of 2E,4E- and 2E,4Z-2,4-dienoic acid isomers (solid, 11%). MS: m/e 667.5 (M+H)+, 2.41 min (method 5). For 2E,4E isomer, 1H NMR (400 MHz, CHLOROFORM-d) δ 7.40-7.26 (m, 1H), 6.54 (d, J=15.1 Hz, 1H), 6.18 (dd, J=15.3, 11.0 Hz, 1H), 5.88 (d, J=15.1 Hz, 1H), 5.65 (s., 1H), 4.80 (s, 1H), 4.66 (s, 1H), 3.22-2.63 (m, 12H), 2.21-0.81 (m, 23H), 1.71 (s, 3H), 1.13 (s, 3H), 1.01 (s, 3H), 0.99 (s, 3H), 0.91 (s, 3H), 0.71 (s, 3H).

Workup

custom5-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)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)penta-2,4-dienoic acid was prepared

Sources & evidence

ORD record: ord-06fa54e51be744359c0e36633f7f1b81
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249180B2

Reaction notes

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