Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 25893

Reaktionsgleichung

Reaktionsgleichung von HRID 25893
[CH:1]1([N:7]=[C:8]=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(NCC(N1CCC[C@H]1C(O)=O)=O)(OC(C)(C)C)=[O:17]>C1COCC1>[CH:10]1([NH:9][C:8](=[O:17])[NH:7][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Komponenten

4

Edukt 2

HCID 10868DicyclohexylcarbodiimideHCID 11673468Boc-gly-pro-OH

Produkt 1

HCID 4277N,N'-Dicyclohexylurea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A portion (10.3g= 0.05 mole) of dicyclohexylcarbodiimide (DCC) was added dropwise under stirring at 0° C. to a solution of N-Boc-glycyl-L-proline prepared in accordance with the method described in J. Chem. Soc. (C), 954 (1969) (27.2g= 0.1 mole) in dried THF (100ml) and the reaction mixture was kept under continuous stirring for 45 minutes. To the filtrate obtained by filtering-off of dicyclohexyl urea precipitated in the mixture, was added at 0° C. a solution of 7-amino-4-methylcoumarin (8.75g= 0.05 mole) in dimethylformamide (DMF) (60ml). After standing overnight at room temperature, the reaction mixture was concentrated in vacuo to give a residue which was dissolved in ethyl acetate (300ml.). The solution was washed successively with 1 N hydrochloric acid, aqueous 5% sodium bicarbonate and water, dried with anhydrous magnesium sulfate, and concentrated in vacuo. The residue was recrystallized from a binary mixture of ethyl acetate (150ml) and n-hexance (70ml) to give 20.1g (yield, 93.4%) of crystalline 7-(n-BOC-glycyl-L-prolyl)-amino-4-methylcoumarin.

Aufarbeitung

  1. customprepared in accordance with the method

Quellen und Nachweise

ORD-Eintrag
ord-1315159e7b9240e7b0b0a53beb192f40
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04147692

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