Borane → tert-Butyl 2-hydroxyethyl(2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate

HRID 1917176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1917176
[OH:1][CH2:2][CH2:3][N:4]([CH2:12][C:13]([N:15]1[CH2:20][CH2:19][S:18][C:17]2[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:16]1=2)=O)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].B>C1COCC1>[OH:1][CH2:2][CH2:3][N:4]([CH2:12][CH2:13][N:15]1[CH2:20][CH2:19][S:18][C:17]2[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:16]1=2)[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8]

Komponenten

4

Edukt 2

HCID 6331BoraneHCID 59144172tert-Butyl 2-hydroxyethyl(2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)-2-oxoethyl)carbamate

Produkt 1

HCID 59144107tert-Butyl 2-hydroxyethyl(2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)ethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of tert-butyl 2-hydroxyethyl(2-(7-nitro-2H-benzo[b][1,4]thiazin-4(3H)-yl)-2-oxoethyl)carbamate (250 mg, 0.629 mmol) in THF (10 mL) was cooled to 0° C. then treated with borane in THF (1M) (6.29 mL, 6.29 mmol). The resulting bright yellow solution was allowed to warm to room temperature and then stirred at this temperature for 2.5 days. The mixture was cooled to 0° C., and the reaction was then carefully quenched with MeOH (dropwise addition at first; 20 mL total). The cooling bath was removed, and the yellow solution was stirred for 20 minutes then concentrated. The orange residue was dissolved in MeOH (50 mL) and concentrated to dryness. This residue was dissolved in EtOAc (20 mL) and filtered through a pad of silica gel. The silica pad was eluted with EtOAc (100 mL). The filtrate was concentrated to give an orange residue which was dried under reduced pressure for 4 hours (230 mg, 95%). 1H-NMR (CDCl3) δ 7.97 (brs, 1H), 7.87 (brd, J=8.7 Hz, 1H), 6.85-6.71 (m, 1H), 3.81 (brs, 5H), 3.61 (brs, 2H), 4.54-3.31 (m, 4H), 3.02 (overlapping t, 2H), 1.47 (brs, 9H); ESI-MS (m/z, %): 406 (M+Na, 60), 384 (MH+, 10), 328 (60), 284 (100).

Aufarbeitung

  1. temperatureThe mixture was cooled to 0° C.
  2. customthe reaction was then carefully quenched with MeOH (
  3. additiondropwise addition at first
  4. customThe cooling bath was removed
  5. stirringthe yellow solution was stirred for 20 minutes
  6. concentrationthen concentrated
  7. dissolutionThe orange residue was dissolved in MeOH (50 mL)
  8. concentrationconcentrated to dryness
  9. dissolutionThis residue was dissolved in EtOAc (20 mL)
  10. filtrationfiltered through a pad of silica gel
  11. washThe silica pad was eluted with EtOAc (100 mL)
  12. concentrationThe filtrate was concentrated
  13. customto give an orange residue which
  14. customwas dried under reduced pressure for 4 hours (230 mg, 95%)

Quellen und Nachweise

ORD-Eintrag
ord-459f10a588ae45149c7625b32c0db84a
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618286B2

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