Iodoacetic Acid → {2-[(tert-butoxycarbonyl)imino]-5-(methoxymethyl)-1,3,4-thiadiazol-3(2H)-yl}acetic acid

HRID 1851714

Reaktionsgleichung

I[CH2:2][C:3]([OH:5])=[O:4].[CH3:6][O:7][CH2:8][C:9]1[S:13][C:12]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:11][N:10]=1.[H-].[Na+]>O1CCCC1>[C:17]([O:16][C:15]([N:14]=[C:12]1[N:11]([CH2:2][C:3]([OH:5])=[O:4])[N:10]=[C:9]([CH2:8][O:7][CH3:6])[S:13]1)=[O:21])([CH3:20])([CH3:19])[CH3:18]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Iodoacetic acid (409.3 g, 2.2 mol, 1.5 eq) is added in one portion to a solution of tert-butyl [5-(methoxymethyl)-1,3,4-thiadiazol-2-yl]carbamate a13 (360 g, 1.47 mol, 1 eq) in tetrahydrofurane (3 l) at room temperature. Sodium hydride (52.8 g, 2.2 mol, 1.5 eq) is then added portionwise, in 30 minutes, at room temperature. The reaction mixture is heated at 60° C. overnight, and the solvent is evaporated under reduced pressure. Water is added to the residue, the solution is acidified to pH=2 with aqueous 6N HCl, then extracted with CH2Cl2. The organic layer is washed with 10% aqueous sodium thiosulfate and evaporated to dryness to afford 455.7 g of {2-[(tert-butoxy-carbonyl)imino]-5-(methoxymethyl)-1,3,4-thiadiazol-3(2H)-yl}acetic acid a14 which is used directly in the next step without any further purification.

Aufarbeitung

customthe solvent is evaporated under reduced pressure
additionWater is added to the residue
extractionextracted with CH2Cl2
washThe organic layer is washed with 10% aqueous sodium thiosulfate
customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag: ord-a5c89827bc5643c2a4dbdcb84fa5fb1c
Quelldatensatz: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08957218B2

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