1-Aminocyclopropane-1-carboxylic acid → 1-[(1-Cyclohexylcarbonyloxy-2-methylpropoxy)carbonylamino]cyclopropanecarboxylic Acid

HRID 492049

Reaktionsgleichung

Reaktionsgleichung von HRID 492049
[CH2:1]1[C:3]([NH2:7])([C:4]([OH:6])=[O:5])[CH2:2]1.[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:7][C:3]2([C:4]([OH:6])=[O:5])[CH2:2][CH2:1]2)=[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 5351-Aminocyclopropane-1-carboxylic acidHCID 866102931-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl cyclohexanecarboxylate

Produkt 1

HCID 247984071-[(1-Cyclohexylcarbonyloxy-2-methylpropoxy)carbonylamino]cyclopropanecarboxylic AcidAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

Following the general procedure for the synthesis of acyloxyalkyl carbamates, ACPC (0.533 g, 5.27 mmol) and 1-(2,5-dioxoazolidinyloxycarbonyloxy)-2-methylpropyl cyclohexanecarboxylate (1.5 g, 4.39 mmol) were reacted in the acetonitrile/water mixture to provide 0.368 g (27% yield) of the title compound (11) as a white powder after work-up and mass-guided preparative HPLC purification. M.p.: 156-158.5° C. 1H NMR (CDCl3, 400 MHz): δ=6.59 (d, 1H), 6.05 (br s, 0.3H), 5.41 (s, 0.7H), 2.38 (m, 1H), 2.13 (m, 1H), 1.96 (d, 2H), 1.78 (m, 2H), 1.6 (m, 3H), 1.44 (m, 2H), 1.23 (m, 5H), 0.99 (m, 6H). MS (ESI) m/z 350.05 (M+Na)+.

Quellen und Nachweise

ORD-Eintrag
ord-8618fd98246145c5ae8593ae8c6eb135
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531572B2

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