Potassium Carbonate → dimethyl 2,2'-(2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(methoxycarbonyl)phenyl)-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]chrysene-3a-carboxamido)ethylazanediyl)diacetate

HRID 2405491Notes

Reaction equation

HRID 2405491 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([C@:7]12[CH2:42][CH2:41][C@@H:40]([C:43]([CH3:45])=[CH2:44])[C@@H:8]1[C@@H:9]1[C@@:22]([CH3:25])([CH2:23][CH2:24]2)[C@@:21]2([CH3:26])[C@@H:12]([C@:13]3([CH3:39])[C@@H:18]([CH2:19][CH2:20]2)[C:17]([CH3:28])([CH3:27])[C:16]([C:29]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][CH:30]=2)=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)=[O:6].Br[CH2:47][C:48]([O:50][CH3:51])=[O:49].C(=O)([O-])[O-:53].[K+].[K+].[O:58]1[CH2:63]CO[CH2:60][CH2:59]1>C(#N)C>[CH3:36][O:35][C:33]([C:32]1[CH:31]=[CH:30][C:29]([C:16]2[C:17]([CH3:27])([CH3:28])[C@H:18]3[C@:13]([CH3:39])([CH2:14][CH:15]=2)[C@@H:12]2[C@:21]([CH3:26])([C@@:22]4([CH3:25])[C@H:9]([CH2:10][CH2:11]2)[C@H:8]2[C@H:40]([C:43]([CH3:45])=[CH2:44])[CH2:41][CH2:42][C@:7]2([C:5]([NH:4][CH2:3][CH2:2][N:1]([CH2:60][C:59]([O:58][CH3:63])=[O:53])[CH2:47][C:48]([O:50][CH3:51])=[O:49])=[O:6])[CH2:24][CH2:23]4)[CH2:20][CH2:19]3)=[CH:38][CH:37]=1)=[O:34]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 60984Methyl bromoacetateHCID 67776312methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-aminoethylcarbamoyl)-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

Product 1

HCID 67777318dimethyl 2,2'-(2-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-9-(4-(methoxycarbonyl)phenyl)-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]chrysene-3a-carboxamido)ethylazanediyl)diacetateYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(2-aminoethylcarbamoyl)-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 (20 mg, 0.033 mmol) in acetonitrile (1 mL) and dioxane (1 mL) was added methyl 2-bromoacetate (14.93 mg, 0.098 mmol) and potassium carbonate (22.48 mg, 0.163 mmol). The reaction mixture was heated up at 78° C. for 3 hours. LCMS indicated the formation of desired product and consumption of starting material. The reaction mixture was quenched with distilled water, extracted with DCM (3×3 mL). All the extracts were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure to provide the desired product (17 mg, 69%) as white solid. LCMS: m/e 759.7 (M+H)+, 2.88 min (method 1).

Workup

  1. customthe formation of desired product and consumption of starting material
  2. customThe reaction mixture was quenched with distilled water
  3. extractionextracted with DCM (3×3 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e5d95e8cf316418784e7e6cd8aa3c3af
Source dataset
uspto-grants-2014_08
Patent number
US08802661B2

Reaction notes

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