Benzyl (S)-(-)-tetrahydro-5-oxo-3-furanylcarbamate → (S)-Benzyl-4-(cyclopropyl(2,3-dichlorobenzyl)amino)-1-hydroxy-4-oxobutan-2-ylcarbamate

HRID 1092798

Reaktionsgleichung

Reaktionsgleichung von HRID 1092798
[Cl:1][C:2]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][NH:5][CH:6]1[CH2:8][CH2:7]1.[O:14]=[C:15]1[O:19][CH2:18][C@@H:17]([NH:20][C:21](=[O:30])[O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:16]1>>[CH2:23]([O:22][C:21](=[O:30])[NH:20][C@@H:17]([CH2:16][C:15]([N:5]([CH:6]1[CH2:7][CH2:8]1)[CH2:4][C:3]1[CH:9]=[CH:10][CH:11]=[C:12]([Cl:13])[C:2]=1[Cl:1])=[O:14])[CH2:18][OH:19])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Komponenten

3

Edukt 2

HCID 697922Benzyl (S)-(-)-tetrahydro-5-oxo-3-furanylcarbamateHCID 834599Cyclopropyl-(2,3-dichloro-benzyl)-amine

Produkt 1

HCID 66593948(S)-Benzyl-4-(cyclopropyl(2,3-dichlorobenzyl)amino)-1-hydroxy-4-oxobutan-2-ylcarbamateAusbeute 52,1 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Into a 100 mL round bottom flask fitted with a reflux condenser and a nitrogen inlet, N-(2,3-dichlorobenzyl)cyclopropanamine (30.3 g, 140.3 mmol) (Example 1A) and (S)-benzyl 5-oxotetrahydrofuran-3-ylcarbamate (22.0 g, 93.5 mmol) were added. The mixture was heated without solvent at 100° C. for 24 hours. Purification by column chromatography (5%->10% MeOH/dichloromethane) gave 22.0 g (52%) of 4A. ESI-MS:m/z 451.3 (M+H)+.

Aufarbeitung

  1. customInto a 100 mL round bottom flask fitted with a reflux condenser and a nitrogen inlet
  2. customPurification by column chromatography (5%->10% MeOH/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-4b9b32a2fe7e492480c31b4bc6c1d522
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129538B1

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