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Water → (7aS,6S)-2-(3,5-dichloro-phenyl)-6-(4-bromophenoxy)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione

HRID 49982
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 49982
CO[C:3](=[O:17])[C@@H:4]1[CH2:8][C@H:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)[CH2:6][NH:5]1.C([O-])([O-])=O.[K+].[K+].[Cl:24][C:25]1[CH:26]=[C:27]([N:32]=[C:33]=[O:34])[CH:28]=[C:29]([Cl:31])[CH:30]=1.O>CN(C=O)C>[Cl:24][C:25]1[CH:26]=[C:27]([N:32]2[C:3](=[O:17])[C@@H:4]3[CH2:8][C@H:7]([O:9][C:10]4[CH:11]=[CH:12][C:13]([Br:16])=[CH:14][CH:15]=4)[CH2:6][N:5]3[C:33]2=[O:34])[CH:28]=[C:29]([Cl:31])[CH:30]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 944603,5-Dichlorophenyl isocyanateHCID 26192761Methyl (2S,4S)-4-(4-bromophenoxy)-2-pyrrolidinecarboxylate

Produkt 1

HCID 9804074(7aS,6S)-2-(3,5-dichloro-phenyl)-6-(4-bromophenoxy)-tetrahydro-pyrrolo[1,2-c]imidazole-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

The compound of formula (II), wherein R11 is 4-bromo, m is 0, W=O, and the bonds depicted as wavy bonds define the 7aS,6S stereoisomer, was prepared as follows. To a solution of cis-4-(4-bromo-phenoxy)-L-proline methyl ester (0.2 g) (0.66 mmol) (Preparation 4) and K2CO3 (0.09 g) (1 eq.) in 10 mL of DMF at 0° C. was added 3,5-dichlorophenyl isocyanate (0.12 g) (1 eq.). The reaction mixture was allowed to warm to 20° C. and was stirred overnight. After adding water, the mixture was extracted with EtOAc. The combined organic extracts were washed with water, dried over MgSO4, and evaporated under reduced pressure to afford after SiO2 chromatography (eluent: DCM), the above-titled compound (60 mg). Mp=116° C. NMR (DMSO, 200 MHz): 7.75 (1H, m), 7.5-7.4 (4H, d+d), 6.85 (2H, d), 5.1 (1H, m), 4.6 (1H, dd), 3.95 (1H, dd), 3.35 (1H, dd), 2.7-2.5 (1H, m), 2.25 (1H, bd).

Aufarbeitung

  1. customwas prepared
  2. extractionthe mixture was extracted with EtOAc
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customto afford after SiO2 chromatography (eluent: DCM)

Quellen und Nachweise

ORD-Eintrag
ord-d08659727858425597f2d5fe8444c906
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06710064B2

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