1-Hydroxybenzotriazole → HCID 19094385, Verbindung

HRID 466232Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 466232
[CH3:1][O:2][P:3]([CH2:7][NH:8][CH:9]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)[C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])([O:5][CH3:6])=[O:4].[CH2:31]([O:38][C:39]([NH:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]O)=[O:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH3:1][O:2][P:3]([CH2:7][NH:8][CH:9]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)[C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][NH:41][C:39]([O:38][CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:40])=[O:16])=[O:11])([O:5][CH3:6])=[O:4]

Komponenten

6

Edukt 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 40724145-(Z-Amino)-1-pentanolHCID 76083370HCID 76083370, Verbindung

Produkt 1

HCID 19094385HCID 19094385, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

The compound of example 12(g) is prepared as follows: N-[2-(dimethylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionic acid (700 mg; 1.61 mmol) in dimethyl formamide (DMF) (10 ml) is treated sequentially with N-benzyloxycarbonyl-5-aminopentanol (400 mg; 1.98 mmol) in DMF (2 ml), 1-hydroxybenzotriazole (HOBT) (265 mg; 1.96 mmol), 4-N,N-dimethylaminopyridine (DMAP) (239 mg; 1.96 mmol) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC) (553 mg; 3.22 mmol). The mixture is stirred for 20 hours, then partitioned between ethyl acetate (50 ml) and 1N HCl(30 ml). The organic layer is washed with a saturated solution of sodium bicarbonate (30 ml), then with brine (30 ml) before being dried over anhydrous sodium sulfate. After concentration under reduced pressure, the oily residue is purified by column chromatography on silica gel, eluting first with ethyl acetate, then with 5% methanol in methylene chloride to yield N-benzyloxycarbonyl-5-aminopentyl N-[2-(dimethylphosphonomethyl amino)-3-(4-biphenylyl)-propionyl]-3-aminopropionate as an oil; Rf(SiO2 ; MeOH/CH2Cl2):0.4.

Aufarbeitung

  1. custompartitioned between ethyl acetate (50 ml) and 1N HCl(30 ml)
  2. washThe organic layer is washed with a saturated solution of sodium bicarbonate (30 ml)
  3. dry with materialwith brine (30 ml) before being dried over anhydrous sodium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe oily residue is purified by column chromatography on silica gel
  6. washeluting first with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-0e607a9af4414bfaa4ea3ad8b58b14fc
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05155100

Notizen zur Reaktion

Wird geladen…