5-Chlorovaleryl chloride → 17-Chloro-6,12-bis(benzyloxy)-7,13-dioxo-6,12-diazaheptadecanenitrile

HRID 2380138Notes

Reaction equation

HRID 2380138 reaction equation
[CH2:1]([O:8][N:9]([C:16](=[O:30])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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.[Cl:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](Cl)=[O:37].C(ON(CCCCC#N)C(=O)CCCCCl)C1C=CC=CC=1>C(Cl)Cl.[OH-].[Na+]>[Cl:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](=[O:37])[N:21]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:20][CH2:19][CH2:18][CH2:17][C:16](=[O:30])[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

6

Reactant 3

HCID 740895-Chlorovaleryl chlorideHCID 10087530N-(Benzyloxy)-N-(4-cyanobutyl)-5-chloropentanamideHCID 103414656,12-Bis(benzyloxy)-7-oxo-6,12-diazadodecanenitrile

Product 1

HCID 1175669117-Chloro-6,12-bis(benzyloxy)-7,13-dioxo-6,12-diazaheptadecanenitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Compound (5) (2.44 g, 5.96 mmol) was reacted with 5-chlorovaleryl chloride (1.13 g, 7.29 mmol) in CH2Cl2 (150 mL) and 1N NaOH (200 mL) by the procedure used for (3). Silica gel column chromatography, eluting with 3% EtOH/CHCl3, gave (6) in quantitative yield as an oil: NMR δ 1.50-1.87 (m, 12H), 2.23-2.53 (m, 6H), 3.47 (t, 2H, J=6), 3.60 (t, 4H, J=6), 4.77 (s, 4H) , 7.33 (s, 10H) . Anal. (C29H38ClN3O4) C, H, N.

Workup

  1. washSilica gel column chromatography, eluting with 3% EtOH/CHCl3

Sources & evidence

ORD record
ord-266f5f1a026846fbaeb9ca936a8e3b98
Source dataset
uspto-grants-1994_11
Patent number
US05364965

Reaction notes

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