(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-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 → HCID 86692377, compound

HRID 1401021Notes

Reaction equation

HRID 1401021 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([CH3:36])([CH3:35])[C@H:9]2[C@:22]([CH3:25])([CH2:23][CH:24]=1)[C@@H:21]1[C@:12]([CH3:34])([C@@:13]3([CH3:33])[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([NH2:32])[CH2:15][CH2:14]3)[CH2:11][CH2:10]2)(=O)=O.CC1(C)C(C)(C)OB([C:47]2[CH2:51][CH2:50][CH:49]([CH2:52][C:53]([O:55][CH3:56])=[O:54])[CH:48]=2)O1>>[NH2:32][C@:16]12[CH2:28][CH2:27][C@@H:26]([C:29]([CH3:31])=[CH2:30])[C@@H:17]1[C@@H:18]1[C@@:13]([CH3:33])([CH2:14][CH2:15]2)[C@@:12]2([CH3:34])[C@@H:21]([C@:22]3([CH3:25])[C@@H:9]([CH2:10][CH2:11]2)[C:8]([CH3:35])([CH3:36])[C:7]([C:47]2[CH2:51][CH2:50][CH:49]([CH2:52][C:53]([O:55][CH3:56])=[O:54])[CH:48]=2)=[CH:24][CH2:23]3)[CH2:20][CH2:19]1

Participants

3

Reactant 2

HCID 71698571(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-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 86692378HCID 86692378, compound

Product 1

HCID 86692377HCID 86692377, compoundYield 55.7%

Procedure

The title compound was prepared as a mixture of diastereomers in 55.7% yield following the method for the preparation of Example 1, Step 1 described above, using (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-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 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopent-2-en-1-yl)acetate as the reactant. MS: m/e 531.5 (M−16)+, 2.69 min (method 3). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.54 (s, 1H), 5.50-5.44 (m, 1H), 4.73 (s, 1H), 4.60 (s, 1H), 3.67 (s, 3H), 3.14 (t, J=7.0 Hz, 1H), 2.81-2.61 (m, 1H), 2.59-2.27 (m, 5H), 2.16-1.96 (m, 4H), 1.79-1.18 (m, 20H), 1.09-1.02 (m, 11H), 0.96 (s, 3H), 0.85 (s, 3H).

Workup

  1. customfor the preparation of Example 1, Step 1
  2. customm/e 531.5 (M−16)+, 2.69 min (method 3)

Sources & evidence

ORD record
ord-5d84f72e74814ad5b4b84d23bf3f8bb9
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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