(1R,3aS,5aR,5bR,7aR,11aR,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 trifluoromethanesulfonate → methyl 1-acetamido-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)cyclohex-3-enecarboxylate

HRID 1401042Notes

Reaction equation

HRID 1401042 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([CH3:48])([CH3:47])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[C@@H:21]1[C@:12]([CH3:46])([C@@:13]3([CH3:45])[C@H:18]([CH2:19][CH2:20]1)[C@H:17]1[C@H:26]([C:29]([CH3:31])=[CH2:30])[CH2:27][CH2:28][C@:16]1([NH:32][CH2:33][CH2:34][N:35]1[CH2:40][CH2:39][CH:38]([S:41]([CH3:44])(=[O:43])=[O:42])[CH2:37][CH2:36]1)[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)(=O)=O.[C:51]([NH:54][C:55]1([C:70]([O:72][CH3:73])=[O:71])[CH2:60][CH2:59][C:58](B2OC(C)(C)C(C)(C)O2)=[CH:57][CH2:56]1)(=[O:53])[CH3:52]>>[C:51]([NH:54][C:55]1([C:70]([O:72][CH3:73])=[O:71])[CH2:60][CH2:59][C:58]([C:7]2[C:8]([CH3:48])([CH3:47])[C@H:9]3[C@:22]([CH3:25])([CH2:23][CH:24]=2)[C@@H:21]2[C@:12]([CH3:46])([C@@:13]4([CH3:45])[C@H:18]([CH2:19][CH2:20]2)[C@H:17]2[C@H:26]([C:29]([CH3:31])=[CH2:30])[CH2:27][CH2:28][C@:16]2([NH:32][CH2:33][CH2:34][N:35]2[CH2:40][CH2:39][CH:38]([S:41]([CH3:44])(=[O:42])=[O:43])[CH2:37][CH2:36]2)[CH2:15][CH2:14]4)[CH2:11][CH2:10]3)=[CH:57][CH2:56]1)(=[O:53])[CH3:52]

Participants

3

Reactant 2

HCID 71698667(1R,3aS,5aR,5bR,7aR,11aR,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 trifluoromethanesulfonateHCID 86692402HCID 86692402, compound

Product 1

HCID 86692404methyl 1-acetamido-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)cyclohex-3-enecarboxylateYield 58.3%

Procedure

The title compound was prepared following the method described in step 1 for the preparation of Example 1, using (1R,3aS,5aR,5bR,7aR,11aR,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 trifluoromethanesulfonate (triflate-2) and methyl 1-acetamido-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enecarboxylate as the reactants. The product was obtained as a mixture of diastereomers in 58.3% yield. MS: m/e 794.6 (M+H)+, 2.718 min (method 8). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.71 (d, J=5.5 Hz, 1H), 5.28 (br. s., 1H), 5.22 (s, 1H), 4.73 (br. s., 1H), 4.60 (br. s., 1H), 3.75 (s, 3H), 3.15 (d, J=10.5 Hz, 2H), 2.92-2.79 (m, 4H), 2.73-2.53 (m, 4H), 2.52-2.22 (m, 7H), 2.20-2.08 (m, 5H), 2.03 (br. s., 1H), 2.00 (d, J=1.8 Hz, 3H), 1.98-1.75 (m, 7H), 1.70 (s, 3H), 1.68-1.20 (m, 15H), 1.14-1.04 (m, 6H), 1.00-0.91 (m, 6H), 0.86 (s, 3H).

Workup

  1. customdescribed in step 1 for the preparation of Example 1
  2. customThe product was obtained as a mixture of diastereomers in 58.3% yield
  3. customm/e 794.6 (M+H)+, 2.718 min (method 8)

Sources & evidence

ORD record
ord-266f4e4d2c364566a08155278c32259a
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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