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

HRID 1798293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798293
O.[CH2:2]([O:4][C:5](=[O:27])[CH2:6][CH:7]1[O:11][B:10]([OH:12])[C:9]2[CH:13]=[C:14]([O:18][C:19]3[S:20][C:21]([N+:24]([O-])=O)=[N:22][N:23]=3)[CH:15]=[C:16]([CH3:17])[C:8]1=2)[CH3:3]>Cl.C(O)C.[Fe]>[CH2:2]([O:4][C:5](=[O:27])[CH2:6][CH:7]1[O:11][B:10]([OH:12])[C:9]2[CH:13]=[C:14]([O:18][C:19]3[S:20][C:21]([NH2:24])=[N:22][N:23]=3)[CH:15]=[C:16]([CH3:17])[C:8]1=2)[CH3:3]

Komponenten

6

Edukt 2

HCID 962WaterHCID 58292621Ethyl 2-(1-hydroxy-4-methyl-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Produkt 1

HCID 58292641Ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetateAusbeute 108,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Concentrated HCl (10 drops) and water (12 ml) were added to a mixture of [6-(5-nitro-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.65 g, 1.71 mmol) and iron powder (0.479 g; 8.55 mmol) in ethanol (30 mL) at room temperature. The resulting mixture was stirred at 85° C. for 1.5 hours, cooled to room temperature and filtered through a pad of celite. The filtrate was evaporated and the residue dissolved in EtOAc (300 mL), washed with brine, dried over Na2SO4 and concentrated to give [6-(5-amino-[1,3,4]thiadiazol-2-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.650 g, 100%) which was used without further purification. 1HNMR (400 MHz, DMSO-d6) δ 9.33 (s, 1H), 7.33 (d, J=12.4 Hz, 1H), 7.18 (d, J=16.8 Hz, 1H), 5.51 (d, J=6.0 Hz, 1H), 4.02 (q, J=7.2 Hz, 2H), 3.10 (d, J=14.4 Hz, 1H), 2.33-2.31 (m, 1H), 2.30 (s, 3H), 1.10 (t, J=7.6 Hz, 3H). MS (ESI) m/z=350 [M+H]+.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. customThe filtrate was evaporated
  4. dissolutionthe residue dissolved in EtOAc (300 mL)
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9bfbf87d5f784bf6a3c4fbcfb8796ab7
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343944B2

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