Triethylamine → HCID 53953833, Verbindung

HRID 256365

Reaktionsgleichung

Reaktionsgleichung von HRID 256365
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C:8]([OH:10])=O.C(N(CC)CC)C.ClC(OCCCC)=O.Br.[NH2:27][CH2:28][C:29]([N:31]1[CH2:35][C:34](=[O:36])[NH:33][C:32]1([CH3:38])[CH3:37])=[O:30]>ClCCl>[CH3:37][C:32]1([CH3:38])[NH:33][C:34](=[O:36])[CH2:35][N:31]1[C:29](=[O:30])[CH2:28][NH:27][C:8](=[O:10])[CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1]

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 61140Butyl chloroformateHCID 31466872-(2-Oxopyrrolidin-1-yl)acetic acidHCID 20163751HCID 20163751, Verbindung

Produkt 1

HCID 53953833HCID 53953833, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

An ice cold solution of 2-oxo-1-pyrrolidineacetic acid (1.03 g) and triethylamine (1.01 ml) in dichloromethane (20 ml) was treated dropwise with butyl chloroformate (0.92 ml). After stirring at 0° C. for 30 minutes a suspension of 1-(2-aminoacetyl)-2,2-dimethyl-4-imidazolidinone hydrobromide (1.82 g) and triethylamine (1.01 ml) in dichloromethane (20 ml) was added, and the temperature was gradually raised to room temperature. After stirring at room temperature for 1 day the suspension was evaporated under reduced pressure. The residue was chromatographed on a silica/gel column eluting with methanol/dichloromethane 1:1. The selected fractions were collected and evaporated, the residue was washed with ethyl acetate and crystallized from ethanol to give the title compound as a white solid, m.p. 229°-231° C.

Aufarbeitung

  1. additionwas added
  2. temperaturethe temperature was gradually raised to room temperature
  3. stirringAfter stirring at room temperature for 1 day the suspension
  4. customwas evaporated under reduced pressure
  5. customThe residue was chromatographed on a silica/gel column
  6. washeluting with methanol/dichloromethane 1:1
  7. customThe selected fractions were collected
  8. customevaporated
  9. washthe residue was washed with ethyl acetate
  10. customcrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-18ff35bc95a545d0bdbc670cb5f779f7
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04703054

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