acetyl-DL-leucine → HCID 178474741, Verbindung

HRID 2286620

Reaktionsgleichung

[C:1]([NH:4][CH:5]([C:10]([OH:12])=O)[CH2:6][CH:7]([CH3:9])[CH3:8])(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[N:40]=[C:39]([OH:41])[C:38]([C:42]([OH:44])=[O:43])=[CH:37][N:36]=2)=[CH:31][CH:30]=1>CN(C)C=O.ClCCl>[C:1]([NH:4][CH:5]([C:10]([NH:28][C:29]1[CH:30]=[CH:31][C:32]([C:35]2[N:40]=[C:39]([OH:41])[C:38]([C:42]([OH:44])=[O:43])=[CH:37][N:36]=2)=[CH:33][CH:34]=1)=[O:12])[CH2:6][CH:7]([CH3:8])[CH3:9])(=[O:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: -10 °C

Versuchsvorschrift

A solution of 13.0 g (75 mmol) of N-acetyl-DL-leucine, 10.5 ml (75 mmol) of triethylamine, and 150 ml of dichloromethane is stirred at -10° C. and 9.75 ml (75 mmol) of isobutyl chloroformate is added. The reaction mixture is stirred for 1/2 hour at -10° C. and a cold solution of 11.6 g (50 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid and 7.7 ml (55 mmol) of triethylamine in 200 ml of dimethylformamide is added. The mixture is stirred at 5° C. for 3 hrs and overnight at room temperature. The reaction mixture is evaporated and the residue treated with water. The pH is lowered to 2.5 with dilute hydrochloric acid and the solid filtered, washed with water, and dried to give 13.8 g of 2-[4-(N-acetyl-DL-leucylamino)-phenyl]-4-hydroxy-5-pyrimidine carboxylic acid; mp 233°-235° C. dec.

Aufarbeitung

stirringThe mixture is stirred at 5° C. for 3 hrs and overnight at room temperature
customThe reaction mixture is evaporated
additionthe residue treated with water
filtrationthe solid filtered
washwashed with water
customdried

Quellen und Nachweise

ORD-Eintrag: ord-016401fa0bb54bdfb534e22972f0eb13
Quelldatensatz: uspto-grants-1981_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04267180

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