6,15-Bis(benzyloxy)-7-oxo-6,15-diazapentadecanenitrile → 23-Bromo-6,15-bis(benzyloxy)-7,16-dioxo-6,15-diazatricosanenitrile

HRID 2380145Notes

Reaction equation

HRID 2380145 reaction equation
[CH2:1]([O:8][N:9]([C:16](=[O:33])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42](Cl)=[O:43].C(ON(CCCCC#N)C(=O)CCCCCl)C1C=CC=CC=1>>[Br:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][C:42](=[O:43])[N:24]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:16](=[O:33])[N:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15]

Participants

4

Reactant 3

HCID 100725246,15-Bis(benzyloxy)-7-oxo-6,15-diazapentadecanenitrileHCID 10087530N-(Benzyloxy)-N-(4-cyanobutyl)-5-chloropentanamideHCID 114022288-bromooctanoyl Chloride

Product 1

HCID 1032699123-Bromo-6,15-bis(benzyloxy)-7,16-dioxo-6,15-diazatricosanenitrile

Procedure

Compound [III] (1.50 g, 3.32 mmol) was combined with 8-bromooctanoyl chloride (0.963 g, 3.99 mmol) following the conditions used for (3). The crude oil was purified by silica gel column chromatography with 1:1 hexane/EtOAc as the eluant, giving 2.06 g (95%) of [IV] as an oil: NMR δ 1.17-2.00 (m, 24H), 2.23-2.50 (m, 6H), 3.36 (t, 2H, J=6), 3.60 (t, 2H, J=6), 3.63 (t, 2H, J=6), 4.77 (s, 4H), 7.33 (s, 10H). Anal. (C35H50BrN3O4) C, H, N.

Workup

  1. customThe crude oil was purified by silica gel column chromatography with 1:1 hexane/EtOAc as the eluant

Sources & evidence

ORD record
ord-7799994d9e684705ba78d3a706c44fb5
Source dataset
uspto-grants-1994_11
Patent number
US05364965

Reaction notes

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