Methyl isothiocyanate → N-[2-chloro-4-(3-methylthioureido)benzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester

HRID 24654

反応式

[CH3:1][N:2]=[C:3]=[S:4].[CH3:5][O:6][C:7](=[O:35])[C@H:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])=[CH:23][CH:22]=1)[NH:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][C:12]=1[Cl:18].CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH3:5][O:6][C:7](=[O:35])[C@H:8]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])=[CH:23][CH:22]=1)[NH:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:3]([NH:2][CH3:1])=[S:4])=[CH:13][C:12]=1[Cl:18]

参加物

反応条件

温度: 90 °C

実験手順

Methylisothiocyanate (43 μL) was added to a solution of N-(4-amino-2-chlorobenzoyl)-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (55.1 mg) in anhydrous DMF (1 mL) containing DIEA (22 μL) and DMAP (catalitic amount). The resulting mixture was then heated at 90° C. under N2 for 1 d. After cooling, the mixture was diluted with EtOAc, washed sequentially with 1N HCl, satd. NaHCO3 and water, dried (MgSO4) and evaporated. The residue was purified by preparative TLC (silica gel) using CH2Cl2/MeOH (15:1) as an eluent to give N-[2-chloro-4-(3-methylthioureido)benzoyl]-4-(2-methoxyphenyl)-L-phenylalanine methyl ester (22.7 mg). ESMS: m/z 512 (MH+).

後処理

temperatureAfter cooling
washwashed sequentially with 1N HCl
dry with materialNaHCO3 and water, dried (MgSO4)
customevaporated
customThe residue was purified by preparative TLC (silica gel)

出典と根拠

ORDレコード: ord-258276ba663a44b99a5259d13e255860
出典データセット: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US06855843B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 3

反応条件

実験手順

後処理

出典と根拠

関連ノート