Triethylamine → (S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamate

HRID 2744

Reaktionsgleichung

Reaktionsgleichung von HRID 2744
[C:1]([C@@H](C)C(N)(N)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[OH2:23].O[N:25]1[C:29]2C=C[CH:32]=[CH:33][C:28]=2[N:27]=N1.Cl.CN(C)CCCN=C=NCC>C1COCC1>[C:4]([O:3][C:1](=[O:2])[NH:27][C@H:28]1[CH2:33][CH2:32][NH:25][C:29]1=[O:23])([CH3:5])([CH3:6])[CH3:7]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86752309(S)-Boc-Diaminobutyric acid

Produkt 1

HCID 10750535(S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamateAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

(S)-Boc-Diaminobutyric acid (25 g, 115 mmol), triethylamine (35 g, 344 mmol), and 1-hydroxybenzotriazole hydrate (19.3 g, 143 mmol) are dissolved in 300 mL of THF. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27.4 g, 143 mmol) is added to the solution. The solution is heated at 60° C. over 15 min. A white precipitate forms and the solution is kept at 60° C. for 4 h. After this time, the solution is filtered and the collected liquid is concentrated. The crude product is purified by column chromatography eluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2 to afford the title compound (19.6 g, 98 mmol) as a white solid.

Aufarbeitung

  1. filtrationAfter this time, the solution is filtered
  2. concentrationthe collected liquid is concentrated
  3. customThe crude product is purified by column chromatography
  4. washeluting with a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-0a8a7f7391de4560854070e9af7b0eeb
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05731315

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