Trifluoroacetic acid → N1-(4-Cyanobutyl)-N1-(phenylmethoxy)-N4-[5-[(phenylmethoxy)amino]pentyl]butanediamide

HRID 1656818Notes

Reaction equation

FC(F)(F)C(O)=O.C(OC([N:15]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:42])[CH2:23][CH2:24][C:25](=[O:41])[N:26]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:27][CH2:28][CH2:29][CH2:30][C:31]#[N:32])=O)(C)(C)C>C(Cl)Cl>[CH2:34]([O:33][N:26]([C:25](=[O:41])[CH2:24][CH2:23][C:22](=[O:42])[NH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][NH:15][O:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)[CH2:27][CH2:28][CH2:29][CH2:30][C:31]#[N:32])[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6,17-Bis(benzyloxy)-7,10-dioxo-6,11,17-triazaheptadecane-nitrile (9) was synthesized by slowly adding trifluoroacetic acid (TFA, 40 mL) to (8) (6.00 g, 10.1 mmol) in CH2Cl2 (100 mL). The solution was stirred at 0° C. for 15 minutes and at room temperature for 30 minutes. Solvents were removed by rotary evaporation, aqueous NaHCO3 was added and the product was extracted into CHCl3. Column chromatography on silica gel, eluting with 5% CH3OH/CHCl3, afforded 4.3 g (87%) of (9): NMR δ 1.2-1.8 (m, 10 H), 2.2-3.3 (m, 10 H), 3.62 (t, 2 H, J=7), 4.63 (s, 2 H), 4.82 (s, 2 H), 5.5 (br s, 1 H), 5.87 (br s, 1 H), 7.15-7.35 (m, 10 H). Anal. calcd. for C28H38N4O4 : C, 67.99; H, 7.74; N, 11.33. Found: C, 67.82; R, 7.79; N, 11.29 [Bergeron at al, Tetrahedron (1989), supra].

Workup

customSolvents were removed by rotary evaporation, aqueous NaHCO3
additionwas added
extractionthe product was extracted into CHCl3
washColumn chromatography on silica gel, eluting with 5% CH3OH/CHCl3

Sources & evidence

ORD record: ord-1fc214964cde47adaa76cfa062a3d757
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254724

Reaction notes

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