Potassium Carbonate → HCID 67777287, compound
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C@:8]12[CH2:43][CH2:42][C@@H:41]([C:44]([CH3:46])=[CH2:45])[C@@H:9]1[C@@H:10]1[C@@:23]([CH3:26])([CH2:24][CH2:25]2)[C@@:22]2([CH3:27])[C@@H:13]([C@:14]3([CH3:40])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:29])([CH3:28])[C:17]([C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)=[O:7].Br[CH2:48][CH2:49][CH2:50][C:51]([O:53][CH3:54])=[O:52].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(#N)C>[CH3:54][O:53][C:51](=[O:52])[CH2:50][CH2:49][CH2:48][NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6]([C@:8]12[CH2:43][CH2:42][C@@H:41]([C:44]([CH3:46])=[CH2:45])[C@@H:9]1[C@@H:10]1[C@@:23]([CH3:26])([CH2:24][CH2:25]2)[C@@:22]2([CH3:27])[C@@H:13]([C@:14]3([CH3:40])[C@@H:19]([CH2:20][CH2:21]2)[C:18]([CH3:29])([CH3:28])[C:17]([C:30]2[CH:31]=[CH:32][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:38][CH:39]=2)=[CH:16][CH2:15]3)[CH2:12][CH2:11]1)=[O:7]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 78 °C
Procedure
A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-aminopropylcarbamoyl)-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)benzoate (30 mg, 0.048 mmol), methyl 4-bromobutanoate (25.9 mg, 0.143 mmol) and potassium carbonate (19.78 mg, 0.143 mmol) in dioxane (1 mL) and Acetonitrile (1 mL) was heated up at 78° C. for 3 hours. LCMS indicated the formation of desired product, the reaction mixture was filtered and the clear solution was purified by prep HPLC to give the title compound as a white solid (10 mg, 29%). LCMS: m/e 729.48 (M+H)+, 2.62 min (method 1).
Sources & evidence
- ORD record
- ord-c906d8cd2a1c4b95bce8b63824e21975
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802661B2
Reaction notes
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