Benzyl Bromide → 2-Benzyloxy-3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-propionic acid ethyl ester

HRID 47818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47818
[CH2:1]([O:3][C:4](=[O:31])[CH:5]([OH:30])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)[CH3:2].[CH2:32](Br)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O>[CH2:1]([O:3][C:4](=[O:31])[CH:5]([O:30][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 7498Benzyl BromideHCID 698837723-{4-[2-(Tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester

Produkt 1

HCID 698843902-Benzyloxy-3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-propionic acid ethyl esterAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester (0.59 mmol, 250 mg) was added anhydrous CsOH (0.885 mmol, 148.6 mg) and freshly dried powdered 4 Angstrom molecular sieves (300 mg) followed by benzyl bromide (4.72 mmol, 0.56 mL). The mixture was allowed to stir for 16 hours. The mixture was poured into water and extracted with diethyl ether (3×). The organic layers were combined, washed with water (2×), brine (2×), dried over Na2SO4, and concentrated to a crude oil. The oil was purified by chromatography on silica gel (Merck silica gel 60, art#9385-3) eluting with 20% ethyl acetate in hexanes to give 2-benzyloxy-3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-propionic acid ethyl ester as a clear oil (180 mg, 58%).

Aufarbeitung

  1. customfreshly dried
  2. extractionextracted with diethyl ether (3×)
  3. washwashed with water (2×), brine (2×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to a crude oil
  6. customThe oil was purified by chromatography on silica gel (Merck silica gel 60, art#9385-3)
  7. washeluting with 20% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3e07f90297aa4b878de31e9c8a0560a4
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699904B2

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