Trifluoroacetic acid → 6,12,18-Tris(benzyloxy)-7,13-dioxo-6,12,18-triazaoctadecanenitrile

HRID 1109846Notes

Reaction equation

HRID 1109846 reaction equation
C(OC([N:8]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:44])[N:14]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:35])[N:20]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[N:26])=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(ON(C(=O)CCCCNOCC1C=CC=CC=1)CCCCC#N)C1C=CC=CC=1>C(Cl)Cl>[CH2:28]([O:27][N:20]([C:19](=[O:35])[CH2:18][CH2:17][CH2:16][CH2:15][N:14]([O:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:13](=[O:44])[CH2:12][CH2:11][CH2:10][CH2:9][NH:8][O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[N:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 103414656,12-Bis(benzyloxy)-7-oxo-6,12-diazadodecanenitrileHCID 1048499118-(tert-Butoxycarbonyl)-6,12,18-tris(benzyloxy)-7,13-dioxo-6,12,18-triazaoctadecanenitrile

Product 1

HCID 99862666,12,18-Tris(benzyloxy)-7,13-dioxo-6,12,18-triazaoctadecanenitrileYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound (7) (2.85 g, 3.99 mmol) in CH2Cl2 was treated with excess TFA following the procedure used for (5). Silica gel column chromatography, eluting with 3:2 EtOAc/hexane gave 1.4 g (57%) of (8) as an oil: NMR δ 1.43-1.83 (m, 12 H), 2.20-2.50 (m, 6 H), 2.90 (t, 2 H, J=6), 3.60 (t, 4 H, J=6), 4.63 (s, 2 H), 4.75 (s, 4 H), 7.28 (s, 5 H) , 7.33 (s, 10 H). Anal. (C36H46N4O5) C, H, N.

Workup

  1. washSilica gel column chromatography, eluting with 3:2 EtOAc/hexane

Sources & evidence

ORD record
ord-2712884e6ca546b2973cd8fafce32d5b
Source dataset
uspto-grants-1994_06
Patent number
US05322961

Reaction notes

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