O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine → N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 3,4-dimethylcyclohexylamide

HRID 330430

反応式

HRID 330430 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:25](O)=[O:26])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:28][CH:29]1[CH:34]([CH3:35])[CH2:33][CH2:32][CH:31]([NH2:36])[CH2:30]1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH3:28][CH:29]1[CH:34]([CH3:35])[CH2:33][CH2:32][CH:31]([NH:36][C:25](=[O:26])[C@H:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:16]=2)[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:30]1

参加物

5

反応物 3

HCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 198243303,4-Dimethylcyclohexanamine

生成物 1

HCID 54300108N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 3,4-dimethylcyclohexylamide収率 84.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine (0.3 g) and 3,4-dimethylcyclohexylamine (0.1 g) were dissolved in dry methylene chloride (30 ml) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.2 g) was added to the solution, followed by stirring at room temperature for 12 hours. According to a conventional post-treatment, N-(t-butyloxycarbonyl)-4-benzyloxy-L-phenylalanine 3,4-dimethylcyclohexylamide (I) (0.32 g) was obtained. The above compound (I) (0.3 g) was allowed to react with 4N-hydrogen chloride/dioxane solution to obtain 4-benzyloxy-L-phenylalanine 3,4-dimethylcyclohexylamide hydrochloride (II) (0.26 g). The above compound (II) (0.26 g) and 4-(t-butyloxycarbonyl)aminomethylbenzoic acid (0.16 g) were dissolved in dry methylene chloride (20 ml)-pyridine solution, and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.15 g) was added to the solution. The reaction was carried out at room temperature for 12 hours. After a conventional post-treatment, N-[4-(t-butyloxycarbonyl)aminomethylbenzoyl]-4-benzyloxy-L-phenylalanine 3,4-dimethylcyclohexylamide (III) (0.23 g) was obtained. The above compound (III) was allowed to react with 4N-hydrogen chloride/dioxane solution to (2 ml) obtain N-(4-aminomethylbenzoyl)-4-benzyloxy-L-phenylalanine 3,4-dimethylcyclohexylamide hydrochloride (0.18 g).

出典と根拠

ORDレコード
ord-f0f8c09654cb48eea515fb05bd9632e6
出典データセット
uspto-grants-1990_01
特許番号
US04895842

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