Cesium carbonate → (6-(5-Carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonic acid

HRID 1798322Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798322
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:13][S:14]([O:17]C)(=[O:16])=[O:15])[O:3]1.Cl[C:20]1[S:24][C:23]([C:25]([NH2:27])=[O:26])=[N:22][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:25]([C:23]1[S:24][C:20]([O:12][C:8]2[CH:9]=[C:10]([CH3:11])[C:5]3[CH:4]([CH2:13][S:14]([OH:17])(=[O:15])=[O:16])[O:3][B:2]([OH:1])[C:6]=3[CH:7]=2)=[N:21][N:22]=1)(=[O:26])[NH2:27]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 123487555-Chloro-1,3,4-thiadiazole-2-carboxamideHCID 58292585Methyl (1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate

Produkt 1

HCID 58292845(6-(5-Carbamoyl-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of methyl (1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate (0.46 g, 1.71 mmol, 1 eq.) and 5-chloro-1,3,4-thiadiazole-2-carboxamide (0.42 g, 2.56 mmol, 1.5 eq.) in 10 ml DMF was added cesium carbonate (2.22 g, 6.82 mmol, 4 eq.) portionwise. The reaction was stirred at room temperature overnight. It was then quenched by water, extracted with EtOAc. The aqueous layer was collected and prep HPLC gave the product as white flakes. 1H NMR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 8.01 (s, 1H), 7.39 (d, J=2.4 Hz, 1H), 7.27 (d, J=2.4 Hz, 1H), 5.42 (d, 7.6 Hz, 1H), 3.04 (dd, J=14.4, 1.2 Hz, 1H), 2.46 (m, 1H), 2.27 (s, 3H).

Aufarbeitung

  1. customIt was then quenched by water
  2. extractionextracted with EtOAc
  3. customThe aqueous layer was collected
  4. customprep HPLC gave the product as white flakes

Quellen und Nachweise

ORD-Eintrag
ord-74a5c80557dc4d56891db6bf9cc65dc5
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

Notizen zur Reaktion

Wird geladen…