Triethylamine → N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-N-(1-oxopentyl)-L-valine methyl ester

HRID 1443313노트

반응식

HRID 1443313 반응식
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]([N:7]([C@H:26]([C:30]([OH:32])=[O:31])[CH:27]([CH3:29])[CH3:28])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[C:21]2[NH:22]N=NN=2)=[CH:13][CH:14]=1)=[O:6].[CH3:33]OC(=O)[C@H](C(C)C)NCC1C=CC(C2C=CC=CC=2C#N)=CC=1.C(Cl)(=O)CCCC.C(N(CC)CC)C>ClCCl>[CH3:33][O:32][C:30](=[O:31])[C@H:26]([CH:27]([CH3:28])[CH3:29])[N:7]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[C:21]#[N:22])=[CH:11][CH:10]=1)[C:5](=[O:6])[CH2:4][CH2:3][CH2:2][CH3:1]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 16744794N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-L-valine methyl esterHCID 178447302HCID 178447302, 화합물

생성물 1

HCID 16744795N-((2'-Cyano(1,1'-biphenyl)-4-yl)methyl)-N-(1-oxopentyl)-L-valine methyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Briefly, the process for the preparation of valsartan comprises of the condensation of N-[(2′-cyanobiphenyl-4-yl)methyl]-(L)-valine methyl ester of Formula II with valeryl chloride of Formula III in the presence of triethylamine and dichloromethane, followed by flash chromatography, to give the compound N-[(2′-cyanobiphenyl-4-yl)methyl]-N-valeryl-(L)-valine methyl ester of Formula IV. The compound of Formula IV on tetrazole formation using tributyltin azide and subsequent hydrolysis using sodium hydroxide, followed by flash chromatography, gives valsartan of Formula I.

출처 및 근거

ORD 기록
ord-cc81514b625a4b96bffa630fcbe18e96
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659406B2

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