Triethylamine → HCID 86612119, Verbindung

HRID 2114841Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114841
[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[CH2:5][NH:6][CH2:7][C:8]1([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:11][CH2:10][CH2:9]1.CCN(CC)CC.[Br:34][CH2:35][C:36](Br)=[O:37]>C1COCC1>[Br:34][CH2:35][C:36]([N:6]([CH2:7][C:8]1([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][CH2:10][CH2:11][CH2:12]1)[CH2:5][C:4]1[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:3]=1[O:2][CH3:1])=[O:37]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 69317052HCID 69317052, Verbindung

Produkt 1

HCID 86612119HCID 86612119, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of tert-butyl 1-{[(2,4-dimethoxybenzyl)amino]methyl}cyclopentyl-carbamate (3.20 g, 8.78 mmol) in anhydrous THF (25 mL) was added Et3N (1.35 mL, 9.65 mmol). The solution was cooled to 0° C., treated with bromoacetyl bromide (0.84 mL, 9.65 mmol), and stirred for 3 h. The reaction was poured into ice water and extracted three times into Et2O. The combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. The resulting crude material was subjected to column chromatography eluting with a gradient of 0-100% EtOAc/hexanes. Collection and concentration of the appropriate fractions afforded the product.

Aufarbeitung

  1. extractionextracted three times into Et2O
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washeluting with a gradient of 0-100% EtOAc/hexanes
  6. customCollection and concentration of the appropriate fractions
  7. customafforded the product

Quellen und Nachweise

ORD-Eintrag
ord-27923f49efd54f78a537f04a4fd1d1a2
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435735B2

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