Diisopropylethylamine → Methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-D-norleucylglycinate

HRID 912891

Reaktionsgleichung

Reaktionsgleichung von HRID 912891
[CH3:1][CH2:2][CH2:3][CH2:4][C@@H:5]([NH:9][C:10]([O:12][CH2:13][CH:14]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[C:6]([OH:8])=O.N=C=N.Cl.[CH3:31][O:32][C:33](=[O:36])[CH2:34][NH2:35].C1C=NC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>ClCCl>[CH:16]1[C:15]2[CH:14]([CH2:13][O:12][C:10]([NH:9][C@@H:5]([C:6]([NH:35][CH2:34][C:33]([O:32][CH3:31])=[O:36])=[O:8])[CH2:4][CH2:3][CH2:2][CH3:1])=[O:11])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]=2[CH:19]=[CH:18][CH:17]=1

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 160435CarbodiimideHCID 181649HOAtHCID 2756111(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)hexanoic acid

Produkt 1

HCID 67401200Methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-D-norleucylglycinate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of fmoc-D-Nle-OH (10 g, 28.3 mmol, Novabiochem) and PS-carbodiimide (33 g, 42.45 mmol, 1.28 mmol/g, Argonaut Technologies Inc.) in dichloromethane (250 mL) was stirred at room temperature for 0.5 h. Then, glycine methyl ester hydrochloride (5.3 g, 42.45 mmol, Aldrich), HOAt (3.8 g, 28.3 mmol, Perseptive Biosystems) and diisopropylethylamine (16 mL, 84.9 mmol, Aldrich) were added and the mixture was stirred at room temperature for 16 h. The mixture was filtered and the resin was washed with dichloromethane (2×70 mL). The filtrate was concentrated in vacuo and the residue was purified by column chromatography, eluting with EtOAc/hexane (1:2) to give the title compound as a yellow solid. MS (ESI, positive ion) m/z: 425 (M+1).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. filtrationThe mixture was filtered
  3. washthe resin was washed with dichloromethane (2×70 mL)
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by column chromatography
  6. washeluting with EtOAc/hexane (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-cbfb95a9ce474838ae6ec552e0699167
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026241B2

Verknüpfte Notizen

Wird geladen…