N-(Benzyloxy)-N-(4-cyanobutyl)-5-chloropentanamide → 14-Bromo-6-(benzyloxy)-7-oxo-6-azatetradecanenitrile

HRID 1109851

반응식

HRID 1109851 반응식
[CH2:1]([O:8][NH:9][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:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25].C(ON(CCCCC#N)C(=O)CCCCCl)C1C=CC=CC=1.CCCCCC.CCOC(C)=O>C(Cl)Cl.[OH-].[Na+]>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](=[O:25])[N:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]#[N:15]

참가 물질

7

반응물 4

HCID 10087530N-(Benzyloxy)-N-(4-cyanobutyl)-5-chloropentanamideHCID 114022288-bromooctanoyl ChlorideHCID 14078488O-Benzyl-N-(4-cyanobutyl)hydroxylamineHCID 21226206Ethyl acetate hexane

생성물 1

HCID 997885514-Bromo-6-(benzyloxy)-7-oxo-6-azatetradecanenitrile

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

Compound 2 (n=4) (3.2 g, 15.7 mmol) was treated with 8-bromooctanoyl chloride (4.55 g, 18.8 mmol) in CH2Cl2 and 1N NaOH following the procedure used for (3). Silica gel column chromatography with 2:1 hexane/EtOAc afforded 3.8 g (59%) of [I] as an oil: NMR δ 1.17-2.00 (m, 14 H), 2.23-2.50 (m, 4 H), 3.37 (t, 2 H, J=6), 3.63 (t, 2 H, J=6), 4.77 (s, 2 H), 7.33 (s, 5 H). Anal. (C20H29BrN2O2) C, H, N.

출처 및 근거

ORD 기록
ord-469186e1e8df4a709aa89694ce671548
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05322961

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