Reaktion #49697

ord-e19022211d8e4c61b6a8a049cc062ce5

Reaktionsgleichung

O=C=O
CO2
C(=NC1CCCCC1)=NC1CCCCC1
DCC
O=C1O[C@H]([C@@H](O)CO)C(O)=C1O
ester C
CCC(=O)O
27
CCC(=O)O
propanoic acid
→
CCC(=O)OC(C)(C)C
tert-butyl propanoate

Edukte

O=C=O
CO2
—
amine
C(=NC1CCCCC1)=NC1CCCCC1
DCC
O=C1O[C@H]([C@@H](O)CO)C(O)=C1O
ester C
—
methane[4]
—
amide
CCC(=O)O
27
CCC(=O)O
propanoic acid

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
DMF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

972-Cascade:methane[4]:(3-oxo-6-oxa-2-azaheptylidyne):(3-oxo-2-azapentylidyne)4 :tert-butyl propanoate (28) was prepared (45%), as a spongy white solid, from 324-acid 27 (5.40 g, 146 μmol), amine 2 (20.00 g, 48.1 mmol), DCC (9.91 g, 48.1 mmol), 1-HBT (6.50 g, 48.1 mmol), and DMF (250 mL) via Procedure A: 10.87 g; mp 138°-142 ° C.; 1H NMR δ1.39 (s, CH3, 8748H), 1.93-2.17 (m, CH2, 5808H); 13C NMR δ28.0 (CH3), 29.5 (CH2CH2, 57.4 (4°CNH), 80.4 (CMe3), 170.4 (CO2), 172.6 (CONH); IR 3310 (NH), 1730 (ester C=O), 1645 (amide C=O), 1155 ester C--O) cm-1. Anal. Calcd for C8745H15064N484O 2432 :C, 63.31; H, 9.15; N, 4.09. Found: C, 63.47; H, 9.31; N, 4.04.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05422379uspto-grants-1995_06