Sulfuryl chloride → 2-{[5-(bis{[4-(tert-butyl)phenyl]sulfonyl}amino)-1-{2-([tert-butyl(dimethyl)silyl]oxy}ethyl}4-{4-methylphenyl}-1H-pyrazol-3-yl]oxy}ethyl acetate

HRID 1062794

Reaktionsgleichung

Reaktionsgleichung von HRID 1062794
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[C:11]([NH2:20])[N:10]([CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25])[N:9]=1)(=[O:3])[CH3:2].[C:31]([C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1)([CH3:34])([CH3:33])[CH3:32].[S:45](Cl)(Cl)(=[O:47])=[O:46].N1C[C:58]2[C:53](=[CH:54]C=CC=2)[CH2:52][C@H]1C(O)=O.C(OCC)(=O)C.[CH3:69][CH2:70][CH2:71][CH2:72][CH2:73][CH3:74]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1.S([O-])([O-])(=O)=O.[Cu+2]>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[C:11]([N:20]([S:45]([C:71]2[CH:70]=[CH:69][C:74]([C:53]([CH3:58])([CH3:54])[CH3:52])=[CH:73][CH:72]=2)(=[O:47])=[O:46])[S:41]([C:38]2[CH:39]=[CH:40][C:35]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:36][CH:37]=2)(=[O:43])=[O:42])[N:10]([CH2:21][CH2:22][O:23][Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:25])[CH3:26])[N:9]=1)(=[O:3])[CH3:2]

Komponenten

9

Edukt 5

HCID 24648Sulfuryl chlorideHCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acidHCID 21226206Ethyl acetate hexaneHCID 234003092-{[5-amino-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

Produkt 1

HCID 222820282-{[5-(bis{[4-(tert-butyl)phenyl]sulfonyl}amino)-1-{2-([tert-butyl(dimethyl)silyl]oxy}ethyl}4-{4-methylphenyl}-1H-pyrazol-3-yl]oxy}ethyl acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 24462Copper SulfateKatalysatorHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 2-{[5-amino-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate (0.35 g) (Preparation 30), 4-(tert-butyl)phenylsulfonyl chloride (0.25 g) and 4-(N,N-dimethyl)aminopyridine (98 mg) in pyridine (4 ml) was stirred at room temperature overnight. Tlc (30:70 ethyl acetate/hexane) indicated a new less polar product had formed, but the reaction appeared to have proceeded only 50% to completion. A further aliquot of the sulfonyl chloride (0.25 g) was added to the reaction mixture and stirring at room temperature was continued for a further 4 days. Tic analysis then indicated complete disappearance of the starting materials and a single new product was observed. The reaction mixture was poured into saturated copper (II) sulfate solution (100 ml) and the aqueous mixture was extracted with ether (2×50 ml). The combined ether extracts were washed with saturated copper (II) sulfate solution (30 ml). The organic extract was dried over magnesium sulfate, filtered and concentrated under reduced pressure to leave a yellow/brown gum. The gum was recrystallised from methanol/water to give the title compound as yellow crystals (325 mg).

Aufarbeitung

  1. customhad formed
  2. extractionthe aqueous mixture was extracted with ether (2×50 ml)
  3. washThe combined ether extracts were washed with saturated copper (II) sulfate solution (30 ml)
  4. extractionThe organic extract
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto leave a yellow/brown gum
  9. customThe gum was recrystallised from methanol/water

Quellen und Nachweise

ORD-Eintrag
ord-e5a66f05f8e946049b7ac6eb4c153997
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962923B2

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