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

HRID 649046ノート

反応式

HRID 649046 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eb61534544b34bdfb5b61227506f5515
出典データセット
uspto-grants-1988_04
特許番号
US04737519

反応ノート

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