Diphosgene → Benzyl 3-(3-isocyanatobenzamido)propionate

HRID 1415679

반응식

HRID 1415679 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 54246722Benzyl 3-(3-isocyanatobenzamido)propionate

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

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).

출처 및 근거

ORD 기록
ord-4a4fb0882bba4ccdb1bd050561552abc
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05908843

연결된 노트

불러오는 중…