Acetonitrile → Carbonic Acid 10,13-dimethyl-17-(1-methyl-3-octadecylcarbamoyl-propyl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 2,5-dioxo-pyrrolidin-1-yl Ester

HRID 1055805

Reaktionsgleichung

Reaktionsgleichung von HRID 1055805
[CH2:1]([NH:19][C:20](=[O:45])[CH2:21][CH2:22][CH:23]([CH:25]1[C:41]2([CH3:42])[CH:28]([CH:29]3[CH:38]([CH2:39][CH2:40]2)[C:37]2([CH3:43])[CH:32]([CH2:33][CH:34]([OH:44])[CH2:35][CH2:36]2)[CH2:31][CH2:30]3)[CH2:27][CH2:26]1)[CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[C:46](=O)([O:55]N1C(=O)CCC1=O)[O:47][N:48]1[C:52](=[O:53])[CH2:51][CH2:50][C:49]1=[O:54].C(N(CC)CC)C.C(#N)C>ClCCl>[O:54]=[C:49]1[CH2:50][CH2:51][C:52](=[O:53])[N:48]1[O:47][C:46](=[O:55])[O:44][CH:34]1[CH2:33][CH:32]2[C:37]([CH3:43])([CH:38]3[CH:29]([CH2:30][CH2:31]2)[CH:28]2[C:41]([CH3:42])([CH:25]([CH:23]([CH3:24])[CH2:22][CH2:21][C:20](=[O:45])[NH:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:26][CH2:27]2)[CH2:40][CH2:39]3)[CH2:36][CH2:35]1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 686366454-(3-Hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic Acid Octadecylamide

Produkt 1

HCID 72260723Carbonic Acid 10,13-dimethyl-17-(1-methyl-3-octadecylcarbamoyl-propyl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 2,5-dioxo-pyrrolidin-1-yl EsterAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Referring to scheme 22, amide 88 (14.5 g, 23 mmol) was dissolved in anhydrous dichloromethane (150 mL). To the solution were added disuccinimidyl carbonate (8.87 g, 34 mmol), triethylamine (15 mL) and acetonitrile (50 mL). The reaction mixture was stirred at room temperature under argon for 6 h and then evaporated dryness. The residue was dissolved in dichloromethane (300 mL). It was washed with saturated NaHCO3 aqueous solution (3×100 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness. Compound 89 (14.3 g, 81%) was obtained as colorless powder after drying in high vacuum, which was directly used for the next step without further purification.

Aufarbeitung

  1. customevaporated dryness
  2. dissolutionThe residue was dissolved in dichloromethane (300 mL)
  3. washIt was washed with saturated NaHCO3 aqueous solution (3×100 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-68f6ef0350274500921c20c3d5fc831f
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394540B2

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