Phthalimide → tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimidopropionate

HRID 1760806Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1760806
[C:1]([O:5][CH2:6][C@H:7]([C:16](O)=O)[NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:4])([CH3:3])[CH3:2].[C:19]1(=[O:29])[NH:23][C:22](=[O:24])[C:21]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:20]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=[O:52]>O1CCCC1>[C:1]([O:5][C:6](=[O:52])[C@H:7]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:16][N:23]1[C:19](=[O:29])[C:20]2=[CH:28][CH:27]=[CH:26][CH:25]=[C:21]2[C:22]1=[O:24])([CH3:2])([CH3:3])[CH3:4]

Komponenten

6

Edukt 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 6992546(R)-3-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

Produkt 1

HCID 18337585tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimidopropionateAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of O-tert-butyl-N-BOC-D-serine (4 g, 15.31 mmol), phthalimide (3.38 g, 22.9 mmol) and triphenyl phosphine (6.03 g, 22.9 mmol) in tetrahydrofuran (120 ml, anhydrous) was added diisopropyl azodicarboxylate (4.5 ml, 22.9 mmol). The mixture was stirred under nitrogen atmosphere over night. The tetrahydrofuran was removed on the roto-evaporator and the remainder was taken up in methylene chloride (60 ml) and loaded onto a flash silica gel column. Elution with ethyl acetate/hexanes (19%) gave tert-butyl-2(R)-[(tert-butoxycarbonyl)amino]-3-phthalimido-propionate (3.74 g) as a white powder.

Aufarbeitung

  1. customThe tetrahydrofuran was removed on the roto-evaporator
  2. washElution with ethyl acetate/hexanes (19%)

Quellen und Nachweise

ORD-Eintrag
ord-87b689c70e5c40dd84ed6c73d448be8d
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06844366B2

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