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

HRID 1109849Notes

Reaction equation

HRID 1109849 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, 3 H, J=6), 1.13-1.40 (m, 14 H), 1.47-1.90 (m, 12 H), 2.23-2.53 (m, 8 H), 3.50-3.77 (m, 6 H), 4.77 (s, 6 H), 7.33 (s, 15 H). 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-1cf28dfbeaa947d09f23a683925786c7
Source dataset
uspto-grants-1994_06
Patent number
US05322961

Reaction notes

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