Cesium carbonate → Ethyl 2-(6-(5-carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

HRID 1798314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798314
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH:6]1[O:10][B:9]([OH:11])[C:8]2[CH:12]=[C:13]([OH:17])[CH:14]=[C:15]([CH3:16])[C:7]1=2)[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:26]1[S:30][C:29]([C:31]([NH2:33])=[O:32])=[N:28][N:27]=1>CN(C=O)C>[C:31]([C:29]1[S:30][C:26]([O:17][C:13]2[CH:14]=[C:15]([CH3:16])[C:7]3[CH:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:18])[O:10][B:9]([OH:11])[C:8]=3[CH:12]=2)=[N:27][N:28]=1)(=[O:32])[NH2:33]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 123487555-Chloro-1,3,4-thiadiazole-2-carboxamideHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Produkt 1

HCID 58292581Ethyl 2-(6-(5-carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (3.2 mmol) in anhydrous DMF (8 mL) was added cesium carbonate (8 mmol) and 5-chloro-1,3,4-thiadiazole-2-carboxamide (3.2 mmol). The resulting mixture was stirred at room temperature overnight then quenched with crushed ice. The pH was adjusted to 2 with 6M HCl and the mixture extracted with EtOAc (2×200 mL). The organic extracts were washed with water, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel flash column chromatography (0-75% EtOAc in hexane) to give ethyl 2-(6-(5-carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate.

Aufarbeitung

  1. customthen quenched with crushed ice
  2. extractionthe mixture extracted with EtOAc (2×200 mL)
  3. washThe organic extracts were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel flash column chromatography (0-75% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b2ef53838fa54356b6dacd83908bfe99
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

Notizen zur Reaktion

Wird geladen…