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Benzyl Bromide → Methyl 2-benzyl-3-hydroxypropanoate

HRID 356871
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 356871
[OH:1][CH2:2][CH2:3][C:4]([O:6][CH3:7])=[O:5].C([N-]C(C)C)(C)C.[Li+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([CH:3]([CH2:2][OH:1])[C:4]([O:6][CH3:7])=[O:5])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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Komponenten

4

Edukt 3

HCID 7498Benzyl BromideHCID 80252Propanoic acid, 3-hydroxy-, methyl esterHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 10702975Methyl 2-benzyl-3-hydroxypropanoate

Versuchsvorschrift

β-Propiolactone (A) is dissolved in methanol and treated with 1 equivalent of triethylamine to produce methyl 3-hydroxypropionate (B). Compound B is converted to the dianion with 2 equivalents of lithium diisopropylamide and alkylated with 1 equivalent of benzyl bromide to produce methyl 2-benzyl-3-hydroxypropionate (C). Compound C is protected as the t-butyldimethylsilyl ether (D). Compound D is then saponified with potassium hydroxide and carefully acidified to produce the acid (E). The acid (E) is then dissolved in tetrahydrofuran, treated with 1 equivalent of N-methylmorpholine and cooled to -20° C. One equivalent of isobutyl chloroformate is added, followed by 1 equivalent of 5,6-diamino-1,3-dipropyluracil in dimethyl-formamide to produce the amide. The amide is then treated with aqueous potassium hydroxide at 70° C. to produce the cyclized, deprotected 3,7-dihydro-8[(R)-1-methyl-2-phenyl-ethyl]1, 3-dipropyl-1H-purine-2,6-dione. ##STR8##

Quellen und Nachweise

ORD-Eintrag
ord-35f8c41bee5b408ea49f18aaab3ad9cc
Quelldatensatz
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05840729

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