1-Hydroxybenzotriazole → 5-Fluoro-4-hydroxy-3-{2-[(1H-imidazole-2-carbonyl)-amino]-propionylamino}-pentanoic acid tert-butyl ester

HRID 491970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491970
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=O)=[O:7].[C:14]([O:18][C:19](=[O:27])[CH2:20][CH:21]([NH2:26])[CH:22]([OH:25])[CH2:23][F:24])([CH3:17])([CH3:16])[CH3:15].C(N(C(C)C)CC)(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>C1COCC1.CN(C1C=CN=CC=1)C>[C:14]([O:18][C:19](=[O:27])[CH2:20][CH:21]([NH:26][C:10](=[O:12])[CH:9]([NH:8][C:6]([C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)=[O:7])[CH3:13])[CH:22]([OH:25])[CH2:23][F:24])([CH3:17])([CH3:15])[CH3:16]

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 108566723-Amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl esterHCID 57462012(2S)-2-[(1H-imidazole-2-carbonyl)-amino]-propionic acid

Produkt 1

HCID 670587205-Fluoro-4-hydroxy-3-{2-[(1H-imidazole-2-carbonyl)-amino]-propionylamino}-pentanoic acid tert-butyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (2S)-2-[(1H-imidazole-2-carbonyl)-amino]-propionic acid and 3-amino-5-fluoro-4-hydroxy-pentanoic acid tert-butyl ester (0.254 g) in THF (7 mL) was cooled to 0° C. before addition of DMAP (0.151 g), diisopropylethyl amine (0.56 mL), HOBT (0.16 g) and EDC HCl (0.23 g). The reaction mixture was stirred at ambient temperature for 18 hrs before being concentrated at reduced pressure. The residue was purified by silica gel chromatography (5% methanol in dichloromethane) to afford the sub-title compound as a colourless solid (0.386 g, 97%): 1H NMR 400 MHz CDCl3/CD3OD 1.40 (12H, m), 3.92 (1H, m), 4.20-4.55 (4H, m), 7.11 (2H, d, J 15); 19F NMR CDCl3-229.74 (m), −229.84 (m), −230.54 (m), −230.87 (m).

Aufarbeitung

  1. concentrationbefore being concentrated at reduced pressure
  2. customThe residue was purified by silica gel chromatography (5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-299548a2bc08420fa7720f524516d7bf
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531570B2

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