Trifluoroacetic acid → 6,15-Bis(benzyloxy)-7-oxo-6,15-diazapentadecanenitrile

Participants

Role	Name	HCID	Charge
Reactant	Trifluoroacetic acid	HCID 6422	—
Reactant	15-(tert-Butoxycarbonyl)-6,15-bis(benzyloxy)-7-oxo-6,15-diazapentadecanenitrile	HCID 10415191	—
Reactant	6,12,18-Trihydroxy-7,13,19-trioxo-6,12,18-triazaoctacosanamine hydrochloride	HCID 18956665	—
Reactant	Chloroform methanol	HCID 21584188	—
Solvent	Dichloromethane	HCID 6344	—
Product	6,15-Bis(benzyloxy)-7-oxo-6,15-diazapentadecanenitrile	HCID 10072524	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

Excess TFA was added to [II] (2.00 g, 3.63 mmol) in CH2Cl2 at 0° C. The solution was stirred at 0° C. for 30 minutes and at room temperature for 15 minutes, and then the reaction was worked up by the method used for (5). Silica gel column chromatography with 2% MeOH/CHCl3 provided 1.51 g (92%) of [III] as an oil: NMR δ 1.17-1.90 (m, 14H), 2.23-2.50 (m, 4H), 2.90 (t, 2H, J=6), 3.40 (s, 1H), 3.63 (t, 2H, J=6), 4.67 (s, 2H), 4.77 (s, 2H), 7.30 (s, 5H), 7.33 (s, 5H). Anal. (C27H37N3O3) C, H, N.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05364965
Source dataset	uspto-grants-1994_11
ORD ID	ord-aa6f66182884417eab9bf2cc7b34602a
Source note	uspto-grants-1994_11