(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 → ethyl 4-((1R,3aS,5aR,5bR,7aR,11aS,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)-2-methylcyclohexa-1,3-dienecarboxylate

HRID 1401024Notes

Reaction equation

HRID 1401024 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.[CH3:39][C:40]1[CH:45]=[C:44](B2OC(C)(C)C(C)(C)O2)[CH2:43][CH2:42][C:41]=1[C:55]([O:57][CH2:58][CH3:59])=[O:56]>>[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:44]2[CH2:43][CH2:42][C:41]([C:55]([O:57][CH2:58][CH3:59])=[O:56])=[C:40]([CH3:39])[CH:45]=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 86692380Ethyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexa-1,3-dienecarboxylate

Product 1

HCID 86692381ethyl 4-((1R,3aS,5aR,5bR,7aR,11aS,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)-2-methylcyclohexa-1,3-dienecarboxylate

Procedure

The title compound was prepared 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 ethyl 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexa-1,3-dienecarboxylate as reactants. MS: m/e 557.4 (M−16)+, 2.47 min (method 2). 1H NMR (400 MHz, CHLOROFORM-d) δ 5.65 (s, 1H), 5.28 (d, J=5.8 Hz, 1H), 4.72 (s, 1H), 4.59 (s, 1H), 4.25-4.16 (m, 2H), 2.62-2.48 (m, 1H), 2.48-2.34 (m, 2H), 2.31-2.17 (m, 2H), 2.15 (s, 3H), 2.09-1.97 (m, 2H), 1.80-1.35 (m, 17H), 1.35-1.18 (m, 9H), 1.18-1.04 (m, 6H), 1.02-1.00 (s, 3H), 0.96 (s, 3H), 0.89 (s, 3H).

Workup

  1. customfor the preparation of Example 1, Step 1
  2. customm/e 557.4 (M−16)+, 2.47 min (method 2)

Sources & evidence

ORD record
ord-ab3fc31bd56a498ab0e8f8b1856624b4
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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