• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】34055

【品名】2-(pentanimidoylamino)acetic acid

【CA登记号】

【 分 子 式 】C7H14N2O2

【 分 子 量 】158.20044

【元素组成】C 53.15% H 8.92% N 17.71% O 20.23%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XIII)

Several novel syntheses of 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde (XI), a key intermediate in the synthesis of losartan, have been described: 1) Treatment of glycine methyl ester hydrochloride (I) with NaOH in methanol, followed by reaction with methyl pentanimidate (II), gives 2-butyl-4,5-dihydro-1H-imidazol-5-one (III), which is treated with POCl3 to give the 2-butyl-5-chloro-1H-imidazole (IV). Reaction of (IV) with POCl3 and DMF yields the enamine (V), which is finally hydrolyzed with water to 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde (XI), the desired intemediate in the synthesis of losartan. 2) Imidazolinone (III) can also be obtained by cyclization of chloroacetic acid methyl ester (VI), chloroacetyl chloride (VII) or bromoacetyl bromide (VIII) with pentanamidine (IX) by means of NaOH in methanol. 3) Alternatively, imidazolinone (III) can be treated with dimethylformamide dimethylacetal in dichloromethane yielding the enamine (X), which is finally treated with POCl3 and hydrolyzed with water. 4) The reaction of glycine (XI) with methyl pentanimidate (II) in NaOH/MeOH gives amidine (XII), which, without isolation, is treated with POCl3 and DMF at 100 C for 2 h, and then hydrolyzed with water to give the desired 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde. Methyl pentanimidate (II) is obtained treating a solution of valeronitrile in MeOH with HCl gas followed by neutralization with aqueous KOH and extraction with Et2O.

1 Kohr, J.; Griffiths, G.J.; Imwinkelried, R.; Hauck, M.B.; Roten, C.A.; Stucky, G.C.; Novel syntheses of 2-butyl-5-chloro-3H-imidazole-4-carbaldehyde: A key intermediate for the synthesis of the angiotensin II antagonist losartan. J Org Chem 1999, 64, 22, 8084.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 17568 methyl 2-aminoacetate C3H7NO2 详情 详情
(II) 34050 methyl pentanimidoate C6H13NO 详情 详情
(III) 34051 2-butyl-3,5-dihydro-4H-imidazol-4-one C7H12N2O 详情 详情
(IV) 34052 2-butyl-5-chloro-1H-imidazole C7H11ClN2 详情 详情
(V) 34053 N-[(2-butyl-5-chloro-4H-imidazol-4-ylidene)methyl]-N,N-dimethylamine; (2-butyl-5-chloro-4H-imidazol-4-ylidene)-N,N-dimethylmethanamine C10H16ClN3 详情 详情
(VI) 10257 methyl 2-chloroacetate; methyl chloroacetate 96-34-4 C3H5ClO2 详情 详情
(VII) 11296 2-Chloroacetyl chloride; Chloroacetic chloride 79-04-9 C2H2Cl2O 详情 详情
(VIII) 14005 2-Bromoacetyl bromide; Bromoacetyl bromide 598-21-0 C2H2Br2O 详情 详情
(IX) 14576 pentanimidamide 109-51-3 C5H12N2 详情 详情
(X) 34054 2-butyl-5-[(E)-(dimethylamino)methylidene]-3,5-dihydro-4H-imidazol-4-one C10H17N3O 详情 详情
(XI) 13925 2-Butyl-4-chloro-1H-imidazole-5-carbaldehyde 83857-96-9 C8H11ClN2O 详情 详情
(XII) 20436 glycine 56-40-6 C2H5NO2 详情 详情
(XIII) 34055 2-(pentanimidoylamino)acetic acid C7H14N2O2 详情 详情
(XIV) 13921 Pentanenitrile; n-Valeronitrile 110-59-8 C5H9N 详情 详情
Extended Information