Diphosgene → Benzyl 3-(3-isocyanatobenzamido)propionate

HRID 1415679

反応式

HRID 1415679 の反応式
C(N(C(C)C)C(C)C)C.[N+]([O-])(O)=O.C(N1C(C)=CC(C)=N1)(=N)N.[NH2:24][C:25]1[CH:26]=[C:27]([CH:43]=[CH:44][CH:45]=1)[C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34])=[O:29].[O:46]=[C:47](Cl)OC(Cl)(Cl)Cl>O1CCOCC1.O>[N:24]([C:25]1[CH:26]=[C:27]([CH:43]=[CH:44][CH:45]=1)[C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)=[O:34])=[O:29])=[C:47]=[O:46]

参加物

7

反応物 4

HCID 10426DiphosgeneHCID 81531DiisopropylethylamineHCID 1981863,5-Dimethyl-1H-pyrazole-1-carboxamidine mononitrateHCID 10424766HCID 10424766、化合物

生成物 1

HCID 54246722Benzyl 3-(3-isocyanatobenzamido)propionate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

0.17 ml of ethyldiisopropylamine is added to a solution of 201 mg of 1-amidino-3,5-dimethylpyrazole nitrate in 17 ml of dioxane and 5 ml of water and the mixture is stirred for 15 minutes. 357 mg of 3-(3-(piperazin-1-ylcarboxamido)benzamido)propionic acid hydrochloride (FAB 321; obtainable by reacting benzyl 3-(3-aminobenzamido)propionate with diphosgene to give benzyl 3-(3-isocyanatobenzamido)propionate, adding on 1-BOC-piperazine to give benzyl 3-(3-(4-BOC-piperazin-1-ylcarboxamido)benzamido)propionate, cleaving the BOC group with 4 N HCl in dioxane to give benzyl 3-(3-(piperazin-1-ylcarboxamido)benzamido)propionate hydrochloride (FAB 411) and hydrogenolyzing on 5% Pd/C) and a further 0.17 ml of ethyldiisopropylamine are then added, the mixture is boiled for 45 hours and evaporated, the residue is dissolved in water and the solution is washed with ether and then with ethyl acetate and evaporated again to give 3-(3-(4-amidinopiperazin-1-ylcarboxamido)benzamido)propionic acid, m.p. 234° (decomposition).

出典と根拠

ORDレコード
ord-4a4fb0882bba4ccdb1bd050561552abc
出典データセット
uspto-grants-1999_06
特許番号
US05908843

関連ノート

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