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【结 构 式】

【分子编号】37356

【品名】5-[[[(benzyloxy)carbonyl]amino](imino)methyl]-1-benzofuran-2-carboxylic acid

【CA登记号】

【 分 子 式 】C18H14N2O5

【 分 子 量 】338.31964

【元素组成】C 63.9% H 4.17% N 8.28% O 23.65%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(IX)

Pinner reaction of ethyl 5-cyano-2-benzofurancarboxylate (VI) gave imidate (VII) and subsequent treatment with ethanolic ammonia afforded amidine (VIII). After basic hydrolysis of the ester group of (VIII), protection with benzyl chloroformate provided the benzyloxycarbonyl derivative (IX). Coupling of (IX) with aminoester (V) in the presence of EDC and HOBt yielded amide (X). Sequential cleavage of benzyloxycarbonyl and tert-butyl groups orf (X) provided amidino acid (XI), which was finally esterified with EtOH and methanesulfonic acid.

1 Ono, S.; Yoshida, T.; Ashimori, A.; Kosaka, K.; Okada, T.; Maeda, K.; Eda, M.; Mori, F.; Inoue, Y.; Ebisu, H.; Imada, T.; Ikegawa, R.; Wang, F.; Nakamura, N. (Welfide Corporation); Novel fused-ring carboxylic acid cpds. or salt thereof,and medicinal use thereof. EP 0712844; JP 1996053398; JP 1996231548; US 5635527; US 5753670; WO 9533720 .
2 Nakamura, N.; Imada, T.; Inoue, Y.; Kosaka, K.; Yoshida, T.; Ono, S.; Fukaya, C.; Maeda, K.; Preparation and pharmacological evaluation of novel glycoprotein (Gp) IIb/IIIa antagonists. 2. Condensed heterocyclic derivatives. Chem Pharm Bull 1999, 47, 12, 1694.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(V) 37352 tert-butyl 2-[(4-aminocyclohexyl)oxy]acetate C12H23NO3 详情 详情
(VI) 37353 ethyl 5-cyano-1-benzofuran-2-carboxylate C12H9NO3 详情 详情
(VII) 37354 ethyl 5-[ethoxy(imino)methyl]-1-benzofuran-2-carboxylate C14H15NO4 详情 详情
(VIII) 37355 ethyl 5-[amino(imino)methyl]-1-benzofuran-2-carboxylate C12H12N2O3 详情 详情
(IX) 37356 5-[[[(benzyloxy)carbonyl]amino](imino)methyl]-1-benzofuran-2-carboxylic acid C18H14N2O5 详情 详情
(X) 37357 ethyl 2-([4-[([5-[[[(benzyloxy)carbonyl]amino](imino)methyl]-1-benzofuran-2-yl]carbonyl)amino]cyclohexyl]oxy)acetate C28H31N3O7 详情 详情
(XI) 37358 2-([4-[([5-[amino(imino)methyl]-1-benzofuran-2-yl]carbonyl)amino]cyclohexyl]oxy)acetic acid C18H21N3O5 详情 详情

合成路线2

该中间体在本合成路线中的序号:(IV)

Pinner reaction of ethyl 5-cyano-2-benzofurancarboxylate (I) gave imidate (II) and subsequent treatment with ethanolic ammonia afforded amidine (III). After basic hydrolysis of the ester group of (III), protection with benzyl chloroformate provided the benzyloxycarbonyl derivative (IV). Coupling of (IV) with ethyl trans-3-(4-aminocyclohexyl)propionate (V) in the presence of EDC and HOBt yielded amide (VI). Finally, hydrogenolysis of the benzyloxycarbonyl protecting group of (VI) provided the title amidino ester.

1 Ono, S.; Yoshida, T.; Ashimori, A.; Kosaka, K.; Okada, T.; Maeda, K.; Eda, M.; Mori, F.; Inoue, Y.; Ebisu, H.; Imada, T.; Ikegawa, R.; Wang, F.; Nakamura, N. (Welfide Corporation); Novel fused-ring carboxylic acid cpds. or salt thereof,and medicinal use thereof. EP 0712844; JP 1996053398; JP 1996231548; US 5635527; US 5753670; WO 9533720 .
2 Nakamura, N.; Imada, T.; Inoue, Y.; Kosaka, K.; Yoshida, T.; Ono, S.; Fukaya, C.; Maeda, K.; Preparation and pharmacological evaluation of novel glycoprotein (Gp) IIb/IIIa antagonists. 2. Condensed heterocyclic derivatives. Chem Pharm Bull 1999, 47, 12, 1694.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
(I) 37353 ethyl 5-cyano-1-benzofuran-2-carboxylate C12H9NO3 详情 详情
(II) 37354 ethyl 5-[ethoxy(imino)methyl]-1-benzofuran-2-carboxylate C14H15NO4 详情 详情
(III) 37355 ethyl 5-[amino(imino)methyl]-1-benzofuran-2-carboxylate C12H12N2O3 详情 详情
(IV) 37356 5-[[[(benzyloxy)carbonyl]amino](imino)methyl]-1-benzofuran-2-carboxylic acid C18H14N2O5 详情 详情
(V) 37352 tert-butyl 2-[(4-aminocyclohexyl)oxy]acetate C12H23NO3 详情 详情
(VI) 37357 ethyl 2-([4-[([5-[[[(benzyloxy)carbonyl]amino](imino)methyl]-1-benzofuran-2-yl]carbonyl)amino]cyclohexyl]oxy)acetate C28H31N3O7 详情 详情
Extended Information