Triethylamine → HCID 86605382, Verbindung

HRID 1180442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180442
[C:1]([OH:9])(=O)[C@H:2]([CH2:4][CH:5]([CH3:7])[CH3:6])[OH:3].Cl.[NH2:11][CH2:12][C:13]#[N:14].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O.CCCCCC>[C:12]([CH2:13][NH:14][C:1](=[O:9])[C@@H:2]([OH:3])[CH2:4][CH:5]([CH3:6])[CH3:7])#[N:11]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 83697Leucic acid, L-HCID 516892Sodium BicarbonateHCID 11491918Aminoacetonitrile hydrochloride

Produkt 1

HCID 86605382HCID 86605382, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

L-leucic acid (85 g, 0.643 mole), amino acetonitrile hydrochloride (68 g, 0.734 mole, 1.14 eg), pyBOP (319 g, 0.612 mole, 0.95 eg) were mixed together in DMF (1 L) and cooled at 0° C. Triethylamine (149 g, 1.47 mole, 2.4 eg) was added dropwise at a rate to maintain internal temperature ≦20° C. Reaction mixture was then allowed to warm to room temperature and stirred for 18 hours. Reaction mixture was poured portionwise into saturated NaHCO3 (4 L) and extracted with EtOAc (2×1 L). Half saturated NaCl solution was added to help partition. Combined organic fractions were washed with brine, 0.5 N HCl, brine, dried and evaporated to give a dark red oil. The latter was passed through a silica plug with 50% EtOAc/hexane to give of the title compound.

Aufarbeitung

  1. temperatureto maintain internal temperature ≦20° C
  2. customReaction mixture
  3. temperatureto warm to room temperature
  4. customReaction mixture
  5. extractionextracted with EtOAc (2×1 L)
  6. additionHalf saturated NaCl solution was added
  7. customto help partition
  8. washCombined organic fractions were washed with brine, 0.5 N HCl, brine
  9. customdried
  10. customevaporated
  11. customto give a dark red oil

Quellen und Nachweise

ORD-Eintrag
ord-45c0a8ce5ce0442d91c2be7ad1a2d3cb
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07279478B2

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