Triethylamine → 4-[3-(Pyridin-4-yl)propyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanine

HRID 265885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 265885
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)=[CH:3][CH:2]=1.CCN(CC)CC.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[C:54]1([S:60]([NH:63][C@@H:64]([CH2:68][NH2:69])[C:65]([OH:67])=[O:66])(=[O:62])=[O:61])[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>CN(C=O)C>[N:1]1[CH:2]=[CH:3][C:4]([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:69][CH2:68][C@H:64]([NH:63][S:60]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)(=[O:62])=[O:61])[C:65]([OH:67])=[O:66])=[O:17])=[CH:18][CH:19]=2)=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 10752796(2S)-3-amino-2-(benzenesulfonamido)propanoic AcidHCID 190341454-[3-(Pyridin-4-yl)propyloxy]benzoic acid

Produkt 1

HCID 104579924-[3-(Pyridin-4-yl)propyloxy]benzoyl-2(S)-phenylsulfonylamino-beta-alanineAusbeute 106,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 19-5 (200 mg, 0.78 mmol), NEt3 (0.22 mL, 1.5 mmol), and DMF (4 mL) at ambient temperature was treated with BOP (345 mg, 0.78 mmol). After 3.0 h, NEt3 (0.22 mL, 1.5 mmol) and 19-2 (190 mg, 0.78 mmol) were added. After 20 h, the reaction mixture was concentrated and subjected to flash chromatography (silica, 10/1/1 CH2Cl2 /CH3OH/AcOH) to give impure 19-6 (400 mg). Prep HPLC purification (Delta Pak C-18Å column, 0 to 100% CH3CN/H2O containing 0.1% trifluoroacetic acid) gave pure 19-6 as a whim solid after lyophilization. Rf 0.74 (silica, 10/1/1 CH2Cl2 /CH3OH/AcOH).

Aufarbeitung

  1. waitAfter 20 h
  2. concentrationthe reaction mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-9a3be4b102b74f0a80c4affd98609cfc
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648368

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