Dicyclohexylcarbodiimide → Pentafluorophenyl N-tert-butoxycarbonyl-6-aminohexanoate

HRID 1489412

Reaktionsgleichung

Reaktionsgleichung von HRID 1489412
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[F:17][C:18]1[C:23](O)=[C:22]([F:25])[C:21]([F:26])=[C:20]([F:27])[C:19]=1[F:28].C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[C:4]([O:3][C:1]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][C:23]1[C:22]([F:25])=[C:21]([F:26])[C:20]([F:27])=[C:19]([F:28])[C:18]=1[F:17])=[O:15])=[O:2])([CH3:6])([CH3:7])[CH3:5]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 13041PentafluorophenolHCID 6376026-((tert-Butoxycarbonyl)amino)hexanoic acid

Produkt 1

HCID 3091479Pentafluorophenyl N-tert-butoxycarbonyl-6-aminohexanoateAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of N-Boc-6-aminohexanoic acid (4.78 g, 20.8 mmol) and pentafluorophenol (3.68 g, 20 mmol) in 50 mL of EtOAc was added DCC (4.12 g, 20 mmol). This was allowed to stir for 16 h, and was then filtered and the filtrate evaporated in vacuo to a syrup. On standing, this crystallized to give 7.46 g (94%) of the ester. Rerystallization from isopropanol/1% acetic acid gave 6.26 g of white needles, mp 81°-83° C. 1H NMR (CDCl3) δ 1.4-1.6 (m, 15H, Boc CH3 and internal CH2), 1.8 (m, 2H, CH2CH2CO2), 2.67 (5, J=7.3 Hz, 2H, CH2CO2), 3.1 (m, 2H, NHCH2), 4.5 (b, 1H, NH). 13C NMR (CDCl3) δ 24.38 (C4), 26.00 (C3), 28.39 (Boc CH3), 29.70 (C5), 33.20 (C2), 40.28 (C6), 79 (Boc C), 156 (Boc C=O), 169 (C1). Anal. Calcd for C17H20NO4F5 : C, 51.4; H, 5.1; N, 3.5. Found: C, 51.5; H, 5.0; N, 3.4.

Aufarbeitung

  1. filtrationwas then filtered
  2. customthe filtrate evaporated in vacuo to a syrup
  3. customthis crystallized

Quellen und Nachweise

ORD-Eintrag
ord-32658d8b714645e08b44cb050dc07e41
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05677440

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