Triethylamine → tert-Butyl (3-(methoxyimino)-3-(4-methoxyphenyl)-propanamido)(methylthio)methylenecarbamate

HRID 133790ノート

反応式

HRID 133790 の反応式
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[CH2:5][C:6]([OH:8])=O.[NH2:17][C:18](=[N:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[S:19][CH3:20].CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[CH2:5][C:6]([NH:17][C:18](=[N:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[S:19][CH3:20])=[O:8]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54237411CarbaMic acid, [iMino(Methylthio)Methyl]-, 1,1-diMethylethyl ester (9CI)HCID 589845323-(Methoxyimino)-3-(4-methoxyphenyl)propanoic acid

生成物 1

HCID 72481141tert-Butyl (3-(methoxyimino)-3-(4-methoxyphenyl)-propanamido)(methylthio)methylenecarbamate収率 88.6%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 3-(methoxyimino)-3-(4-methoxyphenyl)propanoic acid (223 mg), tert-butyl amino(methylthio)methylenecarbamate (190 mg), EDAC.HCl (384 mg), DMAP (122 mg) and triethylamine (0.56 mL) in dichloromethane (3 mL) was stirred at room temperature for 12 h. The crude reaction mixture was purified directly by preparative TLC eluting with 35% ethyl acetate/75% hexanes to give the title compound as a yellowish oil (350 mg). HPLC retention time: 2.42 min (method A). MS (ESI) (M+Na)+ 418.18.

後処理

  1. customThe crude reaction mixture
  2. customwas purified directly by preparative TLC
  3. washeluting with 35% ethyl acetate/75% hexanes

出典と根拠

ORDレコード
ord-82c15c6d766446c481efedaa853fc77c
出典データセット
uspto-grants-2008_06
特許番号
US07390925B2

反応ノート

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