1,2-Dichloroethane → HCID 86754341, Verbindung

HRID 583707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583707
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[CH:10]=[CH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1.Cl.[NH2:22][CH2:23][C@H:24]([NH:32][S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[O:35])=[O:34])[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN1CCOCC1>CN(C=O)C>[C:28]([O:27][C:25](=[O:26])[C@@H:24]([NH:32][S:33]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[O:35])=[O:34])[CH2:23][NH:22][C:16](=[O:18])[C:15]1[CH:14]=[CH:13][C:12]([CH:11]=[CH:10][C:2]2[NH:1][C:9]3[C:4]([N:3]=2)=[N:5][CH:6]=[CH:7][CH:8]=3)=[CH:20][CH:19]=1)([CH3:31])([CH3:29])[CH3:30]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 22853534(S)-3-amino-2-benzenesulfonylamino-propionic acid tert-butyl ester hydrochlorideHCID 53849864HCID 53849864, Verbindung

Produkt 1

HCID 86754341HCID 86754341, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A DMF solution (10 mL) containing 31-3 (301 mg, 1.0 mmol) 2-1 (336 mg, 1.0 mmol), HOBT (206 mg, 1.35 mmol), EDC (258 mg, 1.35 mmol) and NMM (440 μl, 4.0 mmol) was stirred under ambient conditions for 18 h. The DMF was evaporated and the residue partitioned between CH2Cl2 and H2O. The organic layer was dried (MgSO4) and concentrated to a yellow gum which was purified by flash chromatography (silica, 4:1, CHCl3 ·NH3 /IPA) to provide impure 31-4 which was rechromatographed (silica, 9:1 EtOAc/IPA) to give 31-4 as a colorless foam.

Aufarbeitung

  1. customThe DMF was evaporated
  2. customthe residue partitioned between CH2Cl2 and H2O
  3. dry with materialThe organic layer was dried (MgSO4)
  4. concentrationconcentrated to a yellow gum which
  5. customwas purified by flash chromatography (silica, 4:1, CHCl3 ·NH3 /IPA)
  6. customto provide impure 31-4 which
  7. customwas rechromatographed (silica, 9:1 EtOAc/IPA)

Quellen und Nachweise

ORD-Eintrag
ord-b14848722f0d4399b5d7f3a79413d3ca
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05929120

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