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

HRID 1716873Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1716873
[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 esterHCID 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-[2,3b]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-28f8573f0dcb44be88582a3079a14c44
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803836B2

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