Trifluoromethanesulfonic anhydride → 1,1-Dimethylethyl 9-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate

HRID 1514225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514225
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[C:17]1[C:27]2[O:26][CH2:25][CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22][C:21]=2[CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:17]1[C:27]2[O:26][CH2:25][CH2:24][N:23]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:22][C:21]=2[CH:20]=[CH:19][CH:18]=1)(=[O:5])=[O:4]

Komponenten

4

Edukt 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 59403444tert-butyl 9-hydroxy-2,3-dihydrobenzo[f][1,4]oxazepine-4(5H)-carboxylate

Produkt 1

HCID 594035221,1-Dimethylethyl 9-{[(trifluoromethyl)sulfonyl]oxy}-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylateAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Trifluoromethanesulfonic anhydride (6.04 ml, 35.7 mmol) was added to an ice cooled solution of 1,1-dimethylethyl 9-hydroxy-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (Preparation 62) (6.32 g, 23.82 mmol) in pyridine (100 ml) and stirred at 0° C. for 2 hrs. The pyridine was evaporated and the residue dissolved in EtOAc. Washed with 2M HCl, sat sodium bicarbonate solution, dried over magnesium sulphate and evaporated to give the title compound (9 g) as a yellow oil. MS (ES): C15H18F3NO6S requires 397; found 298 [M+H−100]+.

Aufarbeitung

  1. customThe pyridine was evaporated
  2. dissolutionthe residue dissolved in EtOAc
  3. washWashed with 2M HCl
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-93f09485a13f4602aae2c2105ba78f00
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222245B2

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