D(-)-Leucinol → (R)-4-[5-Phenylmethylthio-7-(1-hydroxymethyl-3-methyl-butylamino)-thiazolo[4,5-d]pyrimidin-2-ylamino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1831465

Reaktionsgleichung

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][C:17]3[C:22](Cl)=[N:21][C:20]([S:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[N:19][C:18]=3[N:32]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:33][C@@H:34]([CH2:39][OH:40])[CH2:35][CH:36]([CH3:38])[CH3:37]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[S:16][C:17]3[C:22]([NH:33][C@@H:34]([CH2:39][OH:40])[CH2:35][CH:36]([CH3:38])[CH3:37])=[N:21][C:20]([S:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[N:19][C:18]=3[N:32]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

The product from step (a) (50 mg, 0.1 mmol) and D-leucinol (60 mg, 0.5 mmol) were dissolved in anhydrous tetrahydrofuran (3 mL). The solution was heated in a capped reaction tube at 100° C. for 7 days. The crude product was flash chromatographed on silica (gradient eluent—ammonia:ethyl acetate:chloroform, 1:9:90 to 1:49:50). The product was dried in vacuo at room temperature resulting in 44 mg (76% yield) of the title compound as a white solid.

Aufarbeitung

customchromatographed on silica (gradient eluent—ammonia:ethyl acetate:chloroform, 1:9:90 to 1:49:50)
customThe product was dried in vacuo at room temperature

Quellen und Nachweise

ORD-Eintrag: ord-6c03ed6675c84aae92c77af6e961ac21
Quelldatensatz: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07067657B2

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