Triethylamine → 3-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester

HRID 649046노트

반응식

HRID 649046 반응식
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.[CH2:8]([C:10]1[C:19]([CH2:20][CH3:21])=[C:18]([O:22][CH3:23])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]=1O)[CH3:9].Cl.CN([CH:29]([CH3:33])[C:30]([OH:32])=[O:31])C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:6]([N:3]([CH2:33][CH2:29][C:30]([O:32][C:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]([O:22][CH3:23])=[C:19]([CH2:20][CH3:21])[C:10]=1[CH2:8][CH3:9])=[O:31])[CH2:4][CH3:5])[CH3:7]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 126649942,3-Diethyl-4-methoxynaphtholHCID 216146742-Dimethylamino-propionic acid hydrochloride

생성물 1

HCID 571098023-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester수율 51.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Dry methylene chloride (30 ml) and triethylamine (0.33 ml, 2.34 mmole) are added to a mixture of 2,3-diethyl-4-methoxynaphthol (180 mg, 0.78 mmole), dimethylamino propionic acid hydrochloride (2 eq, 283 mg, 1.56 mmole), dicyclohexylcarbodiimide (2 eq, 322 mg, 1.56 mmole) and 4-dimethylaminpyridine (1 eq, 95 mg, 0.78 mmole) at room temperature under argon, and the resulting suspension is stirred at room temperature under argon for two days. The white precipitate is removed by filtration, and the filtrate is concentrated. Thick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane isolates 144 mg (51.8% ) of 3-(N,N-diethylamino) propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester as a colorless oil.

후처리

  1. customThe white precipitate is removed by filtration
  2. concentrationthe filtrate is concentrated
  3. additionThick layer chromatography (silica gel, 2000 micron) developed by a 9:1 mixture of ether and n-hexane

출처 및 근거

ORD 기록
ord-eb61534544b34bdfb5b61227506f5515
출처 데이터셋
uspto-grants-1988_04
특허 번호
US04737519

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