Dichloromethane → 4-(7-Methoxy-benzo[1,3]dioxol-5-yl)-1,1-dioxo-2-o-tolyl-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester

HRID 1069486

Reaktionsgleichung

Reaktionsgleichung von HRID 1069486
[CH3:1][O:2][C:3](=[O:35])[CH2:4][N:5]([S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([C:24]1[CH:32]=[C:31]([O:33][CH3:34])[C:27]2[O:28][CH2:29][O:30][C:26]=2[CH:25]=1)=O)(=[O:15])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12].ClCCl.C(N(CC)CC)C.P([O-])([O-])([O-])=O.[NH4+].[NH4+].[NH4+]>ClC1CC(C(C)C)CCC1(Cl)C>[CH3:1][O:2][C:3]([C:4]1[N:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH3:12])[S:13](=[O:14])(=[O:15])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]=1[C:24]1[CH:32]=[C:31]([O:33][CH3:34])[C:27]2[O:28][CH2:29][O:30][C:26]=2[CH:25]=1)=[O:35]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 159282Ammonium phosphate, tribasicHCID 22965596{[2-(7-Methoxy-benzo[1,3]dioxole-5-carbonyl)-benzenesulfonyl]-o-tolyl-amino}-acetic acid methyl ester

Produkt 1

HCID 155128974-(7-Methoxy-benzo[1,3]dioxol-5-yl)-1,1-dioxo-2-o-tolyl-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21946423DichloromenthaneLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

To a dry 100-mL flask was added {[2-(7-methoxy-benzo[1,3]dioxole-5-carbonyl)-benzenesulfonyl]-o-tolyl-amino}-acetic acid methyl ester (2.0 g, 4.2 mmol), dry 4 angstrom molecular sieves (8 g), and Ti(TfO)2Cl2 (0.56 g, 0.48 mmol). The flask was cooled to −60° C. and dichloromethane (45 mL) was added. A solution of triethylamine (1.35 g, 9.73 mmol) in dichloromenthan (18 mL) was added. The mixture was warmed to 5° C. over 2 hours, followed by refrigeration at 0° C. for 18 hours. The mixture was poured in to 50-mL ammonium phosphate buffer solution (pH 7), stirred 20 minutes, and filtered. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo to an oil. The oil was chromatographed on 150 g silica gel eluted with a mixture of ethyl acetate and hexane (40:60). The appropriate fractions were evaporated in vacuo, and the residue was evaporated to a foam, 1.02 g, 53%. NMR spectra and elemental analysis were consistent with the structure.

Aufarbeitung

  1. temperatureThe mixture was warmed to 5° C. over 2 hours
  2. filtrationfiltered
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil
  7. customThe oil was chromatographed on 150 g silica gel
  8. washeluted with a mixture of ethyl acetate and hexane (40:60)
  9. customThe appropriate fractions were evaporated in vacuo
  10. customthe residue was evaporated to a foam, 1.02 g, 53%

Quellen und Nachweise

ORD-Eintrag
ord-59ca9f0f0ceb41f98217cddf4abb15e2
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06252070B1

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