Acetonitrile → Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethyl Ester

HRID 1055777

Reaktionsgleichung

Reaktionsgleichung von HRID 1055777
[CH2:1]([C:17]1([CH3:34])[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([CH3:33])[C:21]([CH3:32])=[C:22]([O:28][CH2:29][CH2:30][OH:31])[C:23]=2[CH3:27])[O:18]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][CH3:16].[C:35](=O)([O:44]N1C(=O)CCC1=O)[O:36][N:37]1[C:41](=[O:42])[CH2:40][CH2:39][C:38]1=[O:43].C(N(CC)CC)C.C(#N)C>ClCCl>[CH2:1]([C:17]1([CH3:34])[CH2:26][CH2:25][C:24]2[C:19](=[C:20]([CH3:33])[C:21]([CH3:32])=[C:22]([O:28][CH2:29][CH2:30][O:31][C:35](=[O:44])[O:36][N:37]3[C:41](=[O:42])[CH2:40][CH2:39][C:38]3=[O:43])[C:23]=2[CH3:27])[O:18]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][CH3:16]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 676246Di(succinimido) carbonateHCID 593472622-(2-Hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethanol

Produkt 1

HCID 59347260Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester 2-(2-hexadecyl-2,5,7,8-tetramethyl-chroman-6-yloxy)-ethyl EsterAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Compound 17 (10.5 g, 22 mmol) was dissolved in anhydrous dichloromethane (150 mL). To the solution were added disuccinimidyl carbonate (8.45 g, 33 mmol), triethylamine (20 mL) and acetonitrile (50 mL). The reaction mixture was stirred at room temperature under argon for over night 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 18 (10.4 g, 77%) 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-b646edae397e4e37919abe750a39deba
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394540B2

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