Potassium Iodide → methyl 4-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate

HRID 85704Notes

Reaction equation

HRID 85704 reaction equation
[NH2:1][C@:2]12[CH2:37][CH2:36][C@@H:35]([CH:38]([CH3:40])[CH3:39])[C@@H:3]1[C@@H:4]1[C@@:17]([CH3:20])([CH2:18][CH2:19]2)[C@@:16]2([CH3:21])[C@@H:7]([C@:8]3([CH3:34])[C@@H:13]([CH2:14][CH2:15]2)[C:12]([CH3:23])([CH3:22])[C@@H:11]([C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.Cl[CH2:42][CH2:43][N:44]1[CH2:49][CH2:48][S:47](=[O:51])(=[O:50])[CH2:46][CH2:45]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[I-].[K+]>C(#N)C>[O:50]=[S:47]1(=[O:51])[CH2:48][CH2:49][N:44]([CH2:43][CH2:42][NH:1][C@:2]23[CH2:37][CH2:36][C@@H:35]([CH:38]([CH3:40])[CH3:39])[C@@H:3]2[C@@H:4]2[C@@:17]([CH3:20])([CH2:18][CH2:19]3)[C@@:16]3([CH3:21])[C@@H:7]([C@:8]4([CH3:34])[C@@H:13]([CH2:14][CH2:15]3)[C:12]([CH3:22])([CH3:23])[C@@H:11]([C:24]3[CH:25]=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=3)[CH2:10][CH2:9]4)[CH2:6][CH2:5]2)[CH2:45][CH2:46]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 62657Potassium Phosphate, TribasicHCID 189487894-(2-chloroethyl)thiomorpholine1,1-dioxideHCID 71245228HCID 71245228, compound

Product 1

HCID 71245331methyl 4-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)amino)-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoateYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 4-((1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-3a-amino-1-isopropyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate (50 mg, 0.091 mmol), 4-(2-chloroethyl)thiomorpholine 1,1-dioxide (54.1 mg, 0.274 mmol), potassium phosphate (77 mg, 0.365 mmol) and potassium iodide (36.4 mg, 0.219 mmol) in acetonitrile (2 mL) was heated up at 120° C. for 20 hours. The reaction mixture was quenched with distilled water (5 mL), extracted with dichloromethane (3×5 mL), the organic phases were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the crude product as a yellow solid (40 mg, 62%). LCMS: m/e 709.53 (M+H)+, 2.46 min (method 11).

Workup

  1. customThe reaction mixture was quenched with distilled water (5 mL)
  2. extractionextracted with dichloromethane (3×5 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-85b935ad06c44c789a307c5f04e9214d
Source dataset
uspto-grants-2014_09
Patent number
US08846647B2

Reaction notes

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