Ethyl Acetate → (2S,4R)-4-methanesulfonyloxy-2-(thiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37251

Reaktionsgleichung

Reaktionsgleichung von HRID 37251
Br[CH2:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:7][N:6]1[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1)=[O:16])=O.[CH:28]([NH2:30])=[S:29].C(OCC)(=O)C>CO.ClCCl>[CH3:14][S:11]([O:10][C@H:8]1[CH2:7][N:6]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=2)=[O:16])[C@H:5]([C:3]2[N:30]=[CH:28][S:29][CH:2]=2)[CH2:9]1)(=[O:12])=[O:13]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 3005587MethanethioamideHCID 14305067(2S,4R)-2-bromoacetyl-4-methanesulfonyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Produkt 1

HCID 14305075(2S,4R)-4-methanesulfonyloxy-2-(thiazol-4-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of (2S, 4R)-2-bromoacetyl-4-methane-sulfonyloxy-1- (4-nitrobenzyloxycarbonyl)pyrrolidine(1.15 g) in a mixture of methanol (20 ml) and dichloromethane (15 ml) was added thioformamide (453 mg) at room temperature. After stirring at the same temperature for 4 hours, the mixture was poured into ethyl acetate and washed in turn with saturated aqueous sodium bicarbonate and brine. The dried organic layer was evaporated and the resulting oil was crystallized from a mixture of n-hexane and dichloromethane (100:1 V/V) to give (2S, 4R) -4-methanesulfonyloxy-2-(thiazol-4-yl)-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (930 mg).

Aufarbeitung

  1. washwashed in turn with saturated aqueous sodium bicarbonate and brine
  2. customThe dried organic layer was evaporated
  3. customthe resulting oil was crystallized from a mixture of n-hexane and dichloromethane (100:1 V/V)

Quellen und Nachweise

ORD-Eintrag
ord-023370ae923f417cb88f524b72199bb7
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420122

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