HCID 78320689, compound → HCID 86731505, compound

HRID 1773046Notes

Reaction equation

HRID 1773046 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.[CH3:54][C@:55]12[C@@:72]3([CH3:73])[C@@H:63]([C@:64]4([CH3:84])[C@@H:69]([CH2:70][CH2:71]3)[C:68]([CH3:75])([CH3:74])[C:67]([CH:76]=[CH:77][CH:78]=[CH:79][C:80]([O:82]C)=[O:81])=[CH:66][CH2:65]4)[CH2:62][CH2:61][C@@H:60]1[C@H:59]1[C@H:85]([C:88]([CH3:90])=[CH2:89])[CH2:86][CH2:87][C@:58]1([NH:91][CH2:92][CH2:93][N:94]1[CH2:99][CH2:98][CH:97]([S:100]([CH3:103])(=[O:102])=[O:101])[CH2:96][CH2:95]1)[CH2:57][CH2:56]2>>[CH3:54][C@:55]12[C@@:72]3([CH3:73])[C@@H:63]([C@:64]4([CH3:84])[C@@H:69]([CH2:70][CH2:71]3)[C:68]([CH3:74])([CH3:75])[C:67]([CH:76]=[CH:77][CH:78]=[CH:79][C:80]([OH:82])=[O:81])=[CH:66][CH2:65]4)[CH2:62][CH2:61][C@@H:60]1[C@H:59]1[C@H:85]([C:88]([CH3:90])=[CH2:89])[CH2:86][CH2:87][C@:58]1([NH:91][CH2:92][CH2:93][N:94]1[CH2:95][CH2:96][CH:97]([S:100]([CH3:103])(=[O:101])=[O:102])[CH2:98][CH2:99]1)[CH2:57][CH2:56]2

Participants

3

Reactant 2

HCID 78320689HCID 78320689, compoundHCID 86731504HCID 86731504, compound

Product 1

HCID 86731505HCID 86731505, compound

Procedure

5-((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)penta-2,4-dienoic acid was prepared 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, 39%). MS: m/e 695.5 (M+H)+, 2.38 min (method 5). For 2E,4E isomer, 1H NMR (400 MHz, CHLOROFORM-d) δ 7.35-7.24 (m, 1H), 6.50 (d, J=15.3 Hz, 1H), 6.16 (dd, J=15.2, 11.2 Hz, 1H), 5.89 (d, J=15.1 Hz, 1H), 5.60 (s, 1H), 4.82 (s, 1H), 4.66 (s, 1H), 3.38-2.52 (m, 12H), 2.87 (s, 3H), 2.33-0.83 (m, 24H), 1.71 (s, 3H), 1.13 (s, 3H), 0.99 (s, 3H), 0.97 (s, 3H), 0.89 (s, 3H), 0.68 (s, 3H).

Workup

  1. custom5-((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)penta-2,4-dienoic acid was prepared
  2. customwas prepared

Sources & evidence

ORD record
ord-08e123784bfe4f2e8c9b74800c84767a
Source dataset
uspto-grants-2016_02
Patent number
US09249180B2

Reaction notes

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