Decanoyl chloride → 6,12,18-Tris(benzyloxy)-7,13,19-trioxo-6,12,18-triazaoctacosanenitrile

HRID 2380141Notes

Reaction equation

HRID 2380141 reaction equation
[CH2:1]([O:8][N:9]([C:16](=[O:45])[CH2:17][CH2:18][CH2:19][CH2:20][N:21]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:22](=[O:36])[CH2:23][CH2:24][CH2:25][CH2:26][NH:27][O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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.[C:46](Cl)(=[O:56])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55].C(ON(CCCCC#N)C(=O)CCCCCl)C1C=CC=CC=1>C(Cl)Cl.[OH-].[Na+]>[CH2:1]([O:8][N:9]([C:16](=[O:45])[CH2:17][CH2:18][CH2:19][CH2:20][N:21]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:22](=[O:36])[CH2:23][CH2:24][CH2:25][CH2:26][N:27]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:46](=[O:56])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 66982Decanoyl chlorideHCID 99862666,12,18-Tris(benzyloxy)-7,13-dioxo-6,12,18-triazaoctadecanenitrileHCID 10087530N-(Benzyloxy)-N-(4-cyanobutyl)-5-chloropentanamide

Product 1

HCID 104177206,12,18-Tris(benzyloxy)-7,13,19-trioxo-6,12,18-triazaoctacosanenitrileYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Compound (8) (1.20 g, 1.95 mmol) was reacted with decanoyl chloride (0.565 g, 2.96 mmol) in CH2Cl2 and 1N NaOH following the procedure used for (3). Purification by silica gel column chromatography with 2:1 EtOAc/hexane as the eluant provided 1.20 g (80%) of (10) as an oil: NMR δ 0.90 (t, 3H, J=6), 1.13-1.40 (m, 14H), 1.47-1.90 (m, 12H), 2.23-2.53 (m, 8H), 3.50-3.77 (m, 6H), 4.77 (s, 6H), 7.33 (s, 15H). Anal. (C46H64N4O6) C, H, N.

Workup

  1. customPurification by silica gel column chromatography with 2:1 EtOAc/hexane as the eluant

Sources & evidence

ORD record
ord-e7a8532f85b24f89ae537786c1004578
Source dataset
uspto-grants-1994_11
Patent number
US05364965

Reaction notes

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