Thionyl Chloride → (R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

HRID 731551

Reaktionsgleichung

Reaktionsgleichung von HRID 731551
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14]([OH:16])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O>C(OCC)(=O)C>[O:18]=[C:17]1[C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][C:14](=[O:16])[O:19]1

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 5289152(2R)-2-(((benzyloxy)carbonyl)amino)butanedioic acid

Produkt 1

HCID 12416472(R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamateAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A stirred suspension of N-(benzyloxycarbonyl)-D-aspartic acid (14.7 g, 55.1 mmol) in ethyl acetate (100 mL) was treated dropwise with thionyl chloride (40 mL, 511 mmol) and the resulting homogeneous mixture was stirred at room temperature for 16 hours, and concentrated. The resulting solid was triturated in 1:1 diethyl ether/hexanes (200 mL) for 2 hours and filtered. The solid was dried to provide the desired product (13.7 g, 99%).

Aufarbeitung

  1. concentrationconcentrated
  2. customThe resulting solid was triturated in 1:1 diethyl ether/hexanes (200 mL) for 2 hours
  3. filtrationfiltered
  4. customThe solid was dried

Quellen und Nachweise

ORD-Eintrag
ord-4e4a308926e9427e97248689f4001b41
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585858B2

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