Methyl Acrylate → dimethyl 3,3'-(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)dipropanoate

HRID 2405495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2405495
[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].[C:46]([O:50][CH3:51])(=[O:49])[CH:47]=[CH2:48]>CO>[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]([CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:48][CH2:47][C:46]([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]

Komponenten

4

Edukt 2

HCID 7294Methyl Acrylate2×HCID 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

Produkt 1

HCID 67774882dimethyl 3,3'-(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)dipropanoateAusbeute 192,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A mixture 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) and methyl acrylate (8.40 mg, 0.098 mmol) in methanol (1 mL) was stirred at 20° C. for 3 hours. LCMS indicated the mono-substitution. Methyl acrylate (8.40 mg, 0.098 mmol) was added to the reaction mixture again. The reaction mixture was stirred for 16 hours. 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 title compound as a white solid (25 mg, 98%). LCMS: m/e 787.48 (M+H)+, 2.67 min (method 1).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 16 hours
  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

Quellen und Nachweise

ORD-Eintrag
ord-cef122a78f3c49709a8b94aa99353205
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08802661B2

Notizen zur Reaktion

Wird geladen…