1,2-Dichloroethane → HCID 21114343, Verbindung

HRID 501163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501163
[C:1]([O:5][C:6]([N:8]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C@@H:9]([C:25]([OH:27])=O)[CH2:10][CH2:11][C@@H:12]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=1[F:24])[CH:13]([CH2:15][OH:16])[NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]([C@@H:9]1[CH2:10][CH2:11][C@@H:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[F:24])[CH:13]([CH2:15][OH:16])[NH:14][C:25]1=[O:27])[C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 68432014(5S)-N2,N2-bis(tert-Butoxycarbonyl)-5-(2,3-difluorophenyl)-6-(hydroxymethyl)-D-lysine

Produkt 1

HCID 21114343HCID 21114343, VerbindungAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution (5S)-N2,N2-bis(tert-butoxycarbonyl)-5-(2,3-difluorophenyl)-6-(hydroxymethyl)-D-lysine (180 mg, 0.37 mmol) in DCM (5 mL) were added EDC (106 mg, 0.55 mmol) and HOAT (50 mg, 0.37 mmol). After 30 min, NaHCO3 was added, the layers separated and the aqueous phase backwashed with DCM. The combined organics were dried over magnesium sulfate, filtered and concentrated and the residue purified by silica gel chromatography (0%→10% MeOH/DCM) to give the title compound (100 mg). MS 471.1 (M+1).

Aufarbeitung

  1. customthe layers separated
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue purified by silica gel chromatography (0%→10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-fbc3c3a79a1e4fee881d06b1b842bf65
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772224B2

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