Diisopropylethylamine → 4-Amino-n-iodoacetylbenzylamine

HRID 1886836Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1886836
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C1C(=O)N([O:17][C:18]([CH2:20][I:21])=O)C(=O)C1.C(N(CC)C(C)C)(C)C>ClCCl>[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:18](=[O:17])[CH2:20][I:21])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 4278144-AminobenzylamineHCID 3299230Iodoacetic acid N-hydroxysuccinimide ester

Produkt 1

HCID 686735234-Amino-n-iodoacetylbenzylamineAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

FIG. 11 illustrates the synthesis of Mass Tag (2). 4-Amino-benzylamine (Aldrich, 1 mmol), N-succinimidyl iodoacetate (Pierce, 1 mmol), and N,N-diisopropyl ethylamine (DIEA, 100 μL) were mixed in dichloromethane (10 mL) and stirred at room temperature for 1 hr. Solvent was removed under reduced pressure. The product was purified by silica gel column chromatography, eluting with hexane, ethyl acetate (20%-60%), to give 4-amino-N-iodoacetylbenzylamine (62.2% yield). 1H NMR (MeOD): 7.1 (d, 2H), 6.75 (d, 2H), 4.21 (s, 2H), 3.65 (s, 2H). [M+H]+ in MS: 291.0, calculated; 291.0, found.

Aufarbeitung

  1. customSolvent was removed under reduced pressure
  2. customThe product was purified by silica gel column chromatography
  3. washeluting with hexane, ethyl acetate (20%-60%)

Quellen und Nachweise

ORD-Eintrag
ord-00eb269baf404793bd354ab5c3197e58
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501498B2

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