Triethylamine → [1-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl]-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester

HRID 660423Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660423
[Cl-].[CH2:2]([CH:9]([NH3+:28])[CH:10]([OH:27])[CH2:11][N:12]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[O:36]1[CH:40]2[O:41][CH2:42][CH2:43][CH:39]2[CH:38]([O:44][C:45](=O)[O:46]N2C(=O)CCC2=O)[CH2:37]1>>[O:36]1[CH:40]2[O:41][CH2:42][CH2:43][CH:39]2[CH:38]([O:44][C:45](=[O:46])[NH:28][CH:9]([CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:10]([OH:27])[CH2:11][N:12]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:13][CH:14]([CH3:16])[CH3:15])[CH2:37]1

Komponenten

4

Edukt 3

HCID 8471TriethylamineHCID 17981482Carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester2×HCID 685086951-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride

Produkt 1

HCID 66769651[1-Benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl]-carbamic Acid hexahydro-furo[2,3-b]furan-3-yl Ester

Versuchsvorschrift

A solution of 1-benzyl-3-(benzyloxycarbonyl-isobutyl-amino)-2-hydroxy-propyl-ammonium chloride (4) (29.70 g, 72.90 mmol, 1 equiv), triethylamine (22.00 g, 220 mmol, 3 equiv) and carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (19.80 g, 73.00 mmol, 1 equiv) in 120 mL of dichlomethane were stirred at ambient temperature. Due to the incompleteness of the reaction, carbonic acid 2,5-dioxo-pyrrolidin-1-yl ester hexahydro-furo[2,3-b]furan-3-yl ester (5.00 g, 18.43 mmol) was added to the solution. The solution was stirred at room temperature for 24 h. The solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution. The organic layer was dried on MgSO4, filtered, and evaporated to dryness to obtain the desired product as a white solid. (37.04 g, 70.34 mmol, 96.4%). LRMS (ES+): m/z 527 [M+H]+.

Aufarbeitung

  1. additionwas added to the solution
  2. washThe solution was washed twice with 300 mL of water and once with 300 mL of saturated NaHCO3 solution
  3. customThe organic layer was dried on MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-6f08d6f4c62c4e168d2d0442c5aa0486
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084494B2

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