Potassium Carbonate → HCID 67775810, compound

HRID 2405508Notes

Reaction equation

HRID 2405508 reaction equation
[CH3:1][O:2][C:3](=[O:53])[CH2:4][CH2:5][CH2:6][NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]([C@:14]12[CH2:49][CH2:48][C@@H:47]([C:50]([CH3:52])=[CH2:51])[C@@H:15]1[C@@H:16]1[C@@:29]([CH3:32])([CH2:30][CH2:31]2)[C@@:28]2([CH3:33])[C@@H:19]([C@:20]3([CH3:46])[C@@H:25]([CH2:26][CH2:27]2)[C:24]([CH3:35])([CH3:34])[C:23]([C:36]2[CH:45]=[CH:44][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:38][CH:37]=2)=[CH:22][CH2:21]3)[CH2:18][CH2:17]1)=[O:13].C(=O)([O-])[O-].[K+].[K+].O1CCO[CH2:62][CH2:61]1>C(#N)C>[CH2:61]([N:7]([CH2:6][CH2:5][CH2:4][C:3]([O:2][CH3:1])=[O:53])[CH2:8][CH2:9][CH2:10][NH:11][C:12]([C@:14]12[CH2:49][CH2:48][C@@H:47]([C:50]([CH3:52])=[CH2:51])[C@@H:15]1[C@@H:16]1[C@@:29]([CH3:32])([CH2:30][CH2:31]2)[C@@:28]2([CH3:33])[C@@H:19]([C@:20]3([CH3:46])[C@@H:25]([CH2:26][CH2:27]2)[C:24]([CH3:35])([CH3:34])[C:23]([C:36]2[CH:37]=[CH:38][C:39]([C:40]([O:42][CH3:43])=[O:41])=[CH:44][CH:45]=2)=[CH:22][CH2:21]3)[CH2:18][CH2:17]1)=[O:13])[CH3:62]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 67777287HCID 67777287, compound

Product 1

HCID 67775810HCID 67775810, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
78 °C

Procedure

A mixture of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(3-(4-methoxy-4-oxobutylamino)propylcarbamoyl)-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 (10 mg, 0.014 mmol) and potassium carbonate (5.69 mg, 0.041 mmol) in dioxane (1 mL) and acetonitrile (1.000 mL) was heated up at 78° C. for 3 hours, LCMS indicated the formation of desired product. The reaction mixture was quenched with distilled water (2 mL), extracted with DCM (3×2 mL). All the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a colorless oil (10 mg, 96%). LCMS: m/e 757.50 (M+H)+, 2.73 min (method 1).

Sources & evidence

ORD record
ord-bb68d76c079c4cd4929beb7e27188a27
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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