Dimethylamine → methyl N-[1-(benzofuran-5-yl)-2-(dimethylamino)-2-oxoethyl]-L-leucinate

HRID 383975

반응식

HRID 383975 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@@H:10]([NH:21][C@H:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH:24]([CH3:26])[CH3:25])[C:11]([NH:13][C:14]3C=CC=CC=3O)=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[C:31](N1C=CN=C1)(N1C=CN=C1)=S.[NH2+]1C2C=CC=CC=2N=N1.CNC>ClCCl.O1CCCC1.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([NH:21][C@H:22]([C:27]([O:29][CH3:30])=[O:28])[CH2:23][CH:24]([CH3:25])[CH3:26])[C:11]([N:13]([CH3:14])[CH3:31])=[O:12])=[CH:9][C:4]=2[CH:3]=[CH:2]1

참가 물질

8

반응물 4

HCID 674DimethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 52107781H-BenzotriazoliumHCID 45076859methyl N-{(1R)-1-(benzofuran-5-yl)-2-[(2-hydroxyphenyl)amino]-2-oxoethyl}-L-leucinate

생성물 1

HCID 68843329methyl N-[1-(benzofuran-5-yl)-2-(dimethylamino)-2-oxoethyl]-L-leucinate수율 40.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl N-{(1R)-1-(benzofuran-5-yl)-2-[(2-hydroxyphenyl)amino]-2-oxoethyl}-L-leucinate (410 mg) and 1,1′-thiocarbonyldiimidazole (196 mg) in dichloromethane (5 ml) was left to stand for 18 hours. Water (20 □l) was added to the reaction mixture and this was then stirred rapidly for 30 minutes. After this, 1H-Benzotriazolium, 1-[bis(dimethylamino)methylene]-, tetrafluoroborate(1-), 3-oxide (TBTU, 710 mg) and a solution of dimethylamine in tetrahydrofuran (3 ml of 2M solution) were added. The reaction mixture was stirred for a further 18 hours and was then passed down an SPE (5 g, silica) eluting with a gradient (3:1 to 1:2 cyclohexane:ethyl acetate). The required fractions were combined and evaporated to furnish methyl N-[1-(benzofuran-5-yl)-2-(dimethylamino)-2-oxoethyl]-L-leucinate (140 mg).

후처리

  1. stirringThe reaction mixture was stirred for a further 18 hours
  2. washeluting with a gradient (3:1 to 1:2 cyclohexane:ethyl acetate)
  3. customevaporated

출처 및 근거

ORD 기록
ord-803cb25d64644fb1a665e17ac67c23da
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367673B2

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