(1R,3aS,5aR,5bR,7aR,11aR,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 trifluoromethanesulfonate → methyl 1-acetamido-4-((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)cyclohex-3-enecarboxylate

HRID 1401041Notes

Reaction equation

HRID 1401041 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([CH3:46])([CH3:45])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[C@@H:21]1[C@:12]([CH3:44])([C@@:13]3([CH3:43])[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][S:38](=[O:42])(=[O:41])[CH2:37][CH2:36]1)[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)(=O)=O.[C:49]([NH:52][C:53]1([C:68]([O:70][CH3:71])=[O:69])[CH2:58][CH2:57][C:56](B2OC(C)(C)C(C)(C)O2)=[CH:55][CH2:54]1)(=[O:51])[CH3:50]>>[C:49]([NH:52][C:53]1([C:68]([O:70][CH3:71])=[O:69])[CH2:58][CH2:57][C:56]([C:7]2[C:8]([CH3:46])([CH3:45])[C@H:9]3[C@:22]([CH3:25])([CH2:23][CH:24]=2)[C@@H:21]2[C@:12]([CH3:44])([C@@:13]4([CH3:43])[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[CH2:36][CH2:37][S:38](=[O:41])(=[O:42])[CH2:39][CH2:40]2)[CH2:15][CH2:14]4)[CH2:11][CH2:10]3)=[CH:55][CH2:54]1)(=[O:51])[CH3:50]

Participants

3

Reactant 2

HCID 71698666(1R,3aS,5aR,5bR,7aR,11aR,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 trifluoromethanesulfonateHCID 86692402HCID 86692402, compound

Product 1

HCID 86692403methyl 1-acetamido-4-((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)cyclohex-3-enecarboxylateYield 65.7%

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)-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 trifluoromethanesulfonate 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 65.7% yield. MS: m/e 766.8 (M+H)+, 2.72 min (method 3). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.82 (d, J=3.0 Hz, 1H), 5.26 (br. s., 1H), 5.21-5.12 (m, 1H), 4.70 (d, J=2.0 Hz, 1H), 4.58 (d, J=1.3 Hz, 1H), 3.78-3.68 (m, 3H), 3.14-2.90 (m, 7H), 2.75-2.42 (m, 6H), 2.40-2.19 (m, 3H), 2.13-2.05 (m, 1H), 1.98 (d, J=2.0 Hz, 3H), 1.95-1.69 (m, 6H), 1.68 (s, 3H), 1.65-1.30 (m, 7H), 1.25 (m, 11H), 1.10-1.01 (m, 6H), 0.98-0.87 (m, 6H), 0.87-0.83 (m, 3H).

Workup

  1. customdescribed in step 1 for the preparation of Example 1
  2. customThe product was obtained as a mixture of diastereomers in 65.7% yield
  3. customm/e 766.8 (M+H)+, 2.72 min (method 3)

Sources & evidence

ORD record
ord-9cbb41a580af43079f413f58e1f9413e
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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