4-Oxo-pyrrolidine-1,3-dicarboxylic acid diethyl ester → HCID 178473309, Verbindung

HRID 659046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 659046
O=[C:2]1[CH2:6][N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH:3]1[C:12]([O:14]CC)=O.C(=O)(O)O.[NH2:21][C:22]([NH2:24])=[NH:23]>C(O)(C)(C)C>[NH2:24][C:22]1[N:21]=[C:12]([OH:14])[C:3]2[CH2:4][N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][C:2]=2[N:23]=1

Komponenten

4

Edukt 2

HCID 2763144-Oxo-pyrrolidine-1,3-dicarboxylic acid diethyl esterHCID 286947Carbonic acid-guanidine (1:1)

Produkt 1

HCID 178473309HCID 178473309, VerbindungAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

A suspension of intermediate (f) (14.05 g) and guanidine carbonate (g) (16.6 g, 91.9 mmol) was refluxed in t-butanol (147 mL) for about 6 h. The mixture was allowed to cool to ambient temperature for about 2 h. The volatile components were removed under vacuum and water was added. The pH was adjusted to about 6-7 using KHSO4. The resulting slurry was filtered to collect the solids which were washed with water followed by EtOAc. The solids were dried under vacuum to afford intermediate (h) as cream solids (11.9 g, 53.1 mmol) in 87% yield. 1H NMR (400 MHz, DMSO-D6) δ ppm 11.01 (s, 1H), 6.97 (s, 0.5H, possible tautomer), 6.70 (s, 2H), 4.25 (s, 4H), 4.13-4.03 (m, 2H), 1.22 (t, 3H). LCMS (M+H)+: 225.2.

Aufarbeitung

  1. customThe volatile components were removed under vacuum and water
  2. additionwas added
  3. filtrationThe resulting slurry was filtered
  4. customto collect the solids which
  5. washwere washed with water
  6. customThe solids were dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f0b06a73864d4f16b56147d4a0f050d7
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08080556B2

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