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

HRID 1443313ノート

反応式

HRID 1443313 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-cc81514b625a4b96bffa630fcbe18e96
出典データセット
uspto-grants-2010_02
特許番号
US07659406B2

反応ノート

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