Sarcosine → 2-[(1-Cyclohexylcarbonyloxy-2-methylpropoxy)-N-methylcarbonylamino]acetic Acid

HRID 492079

Reaktionsgleichung

Reaktionsgleichung von HRID 492079
N([CH2:3][C:4]([OH:6])=[O:5])C.[CH:7]1([C:13]([O:15][CH:16]([O:20]C(ON2C(=O)CCC2=O)=O)[CH:17]([CH3:19])[CH3:18])=[O:14])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C:31](#[N:33])[CH3:32].[OH2:34]>>[CH:7]1([C:13]([O:15][CH:16]([O:20][N:33]([CH2:3][C:4]([OH:6])=[O:5])[C:31]([CH3:32])=[O:34])[CH:17]([CH3:18])[CH3:19])=[O:14])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Komponenten

4

Edukt 3

HCID 1088SarcosineHCID 18373917Acetonitrile--water (1/1)HCID 866102931-(2,5-Dioxoazolidinyloxycarbonyloxy)-2-methylpropyl cyclohexanecarboxylate

Produkt 1

HCID 247985872-[(1-Cyclohexylcarbonyloxy-2-methylpropoxy)-N-methylcarbonylamino]acetic AcidAusbeute 16 %

Versuchsvorschrift

Following the general procedure for the synthesis of acyloxycarbamates, sarcosine (0.31 g, 3.50 mmol) and 1-(2,5-dioxoazolidinyloxycarbonyloxy)-2-methylpropyl cyclohexanecarboxylate (1.0 g, 2.92 mmol) were reacted in an acetonitrile/water mixture (20 mL) to provide 0.146 g (16% yield) of the title compound (47) as a white, waxy material after work-up and mass-guided preparative HPLC purification. 1H NMR (CDCl3, 400 MHz): δ=6.60 (t, 1H), 4.20-3.82 (m, 2H), 3.01 (d, 3H), 2.39 (m, 1H), 2.15 (m, 1H), 1.98 (br d, 2H), 1.80 (br d, 2H), 1.71 (br s, 1H), 1.53 (m, 2H), 1.32 (m, 3H), 1.01 (2d, 6H). MS (ESI) m/z 337.99 (M+Na)+; 314.02 (M−H)−.

Quellen und Nachweise

ORD-Eintrag
ord-29bdfcd23ab5459ab5698b4107030ed4
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531572B2

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