D-Serine → 2-[(1-Cyclohexylcarbonyloxy-2-methylpropoxy)carbonylamino]-3-hydroxypropanoic Acid

HRID 492070

Reaktionsgleichung

Reaktionsgleichung von HRID 492070
[NH2:1][C@@H:2]([C:5]([OH:7])=[O:6])[CH2:3][OH:4].[CH:8]1([C:14]([O:16][CH:17]([O:21][C:22](ON2C(=O)CCC2=O)=[O:23])[CH:18]([CH3:20])[CH3:19])=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C(#N)C.O>[CH:8]1([C:14]([O:16][CH:17]([O:21][C:22]([NH:1][CH:2]([CH2:3][OH:4])[C:5]([OH:7])=[O:6])=[O:23])[CH:18]([CH3:19])[CH3:20])=[O:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Komponenten

4

Edukt 2

HCID 71077D-SerineHCID 866102931-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl cyclohexanecarboxylate

Produkt 1

HCID 685140242-[(1-Cyclohexylcarbonyloxy-2-methylpropoxy)carbonylamino]-3-hydroxypropanoic AcidAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Versuchsvorschrift

Following the general procedure for the synthesis of acyloxyalkyl carbamates, D-serine (0.40 g, 3.80 mmol) and 1-(2,5-dioxoazolidinyloxycarbonyloxy)-2-methylpropyl cyclohexanecarboxylate (1.0 g, 2.93 mmol) were reacted in the acetonitrile/water mixture to provide 0.091 g (10% yield) of the title compound (34) as a white wax after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.58 (dd, 1H), 6.11 (dd, 1H), 4.42-4.31 (m, 1H), 4.11-3.92 (br dd, 2H), 2.38 (m, 1H), 2.11 (m, 1H), 1.97 (br d, 2H), 1.77 (br d, 2H), 1.6 (br d, 1H), 1.4 (q, 2H), 1.2 (br m, 3H), 0.99 (dd, 6H). MS (ESI) m/z 354.22 (M+Na)+; 330.21 (M−H)−.

Quellen und Nachweise

ORD-Eintrag
ord-98eca7a55f464ccc9d012971ab39f0b8
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531572B2

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