Triphenylphosphine → t-Butyl (2-{4-[3-(4-tolyl-sulfonylamino)-propenyl]-benzoylamino}-phenyl)-carbamate

HRID 1180810

Reaktionsgleichung

Reaktionsgleichung von HRID 1180810
[C:1]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])(OC(C)(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.OC[CH:40]=[CH:41][C:42]1[CH:64]=[CH:63][C:45]([C:46]([NH:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=2[NH:55][C:56](=[O:62])[O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:47])=[CH:44][CH:43]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:15]1([CH3:18])[CH:14]=[CH:13][C:12]([S:9]([NH:8][CH2:1][CH:40]=[CH:41][C:42]2[CH:64]=[CH:63][C:45]([C:46]([NH:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[NH:55][C:56](=[O:62])[O:57][C:58]([CH3:59])([CH3:60])[CH3:61])=[O:47])=[CH:44][CH:43]=2)(=[O:10])=[O:11])=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 688170N-Boc-p-toluenesulfonamideHCID 72479808t-Butyl {2-[4-(3-hydroxy-propenyl)-benzoylamino]-phenyl}-carbamate

Produkt 1

HCID 86602774t-Butyl (2-{4-[3-(4-tolyl-sulfonylamino)-propenyl]-benzoylamino}-phenyl)-carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of N-Boc-4-tolylsulfonamide (221 mg, 0.81 mmol) and PPh3 (427 mg, 1.63 mmol) in anhydrous THF (4 ml) under nitrogen was successively added a solution of compound XVIII (200 mg, 0.54 mmol) in anhydrous THF (1 ml) and diethyl azodicarboxylate (DEAD) (214 μl, 1.36 mmol). After 16 h, the reaction mixture was quenched with water and diluted with AcOEt. After separation the organic layer was successively washed with water and brine, dried over MgSO4, filtered, and concentrated. The crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:40/60) to afford the title compound XVIIg (337 mg).

Aufarbeitung

  1. customthe reaction mixture was quenched with water
  2. additiondiluted with AcOEt
  3. customAfter separation the organic layer
  4. washwas successively washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was then purified by flash chromatography on silica gel (AcOEt/hexane:40/60)

Quellen und Nachweise

ORD-Eintrag
ord-57d4d008feba4e459f148af7837eafeb
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282608B2

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