benzyl (2S)-2-amino-3-methylbutanoate → HCID 11285398, compound

HRID 1362768Notes

Reaction equation

HRID 1362768 reaction equation
CCCCC(N([C@H](C(O)=O)C(C)C)CC1C=CC(C2C=CC=CC=2C2NN=NN=2)=CC=1)=O.Br[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[C:47]2[N:51]([C:52]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[N:50]=[N:49][N:48]=2)=[CH:37][CH:36]=1.[CH2:71]([O:78][C:79](=[O:85])[C@H:80]([CH:82]([CH3:84])[CH3:83])[NH2:81])[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1>>[CH2:71]([O:78][C:79](=[O:85])[C@H:80]([CH:82]([CH3:83])[CH3:84])[NH:81][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[C:47]2[N:51]([C:52]([C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[N:50]=[N:49][N:48]=2)=[CH:37][CH:36]=1)[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1

Participants

4

Reactant 3

HCID 6950584benzyl (2S)-2-amino-3-methylbutanoateHCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazoleHCID 178447302HCID 178447302, compound

Product 1

HCID 11285398HCID 11285398, compound

Procedure

According to U.S. Pat. No. 5,399,578, Valsartan can also be prepared by reaction of 4-bromomethyl-2′-(1-triphenylmethyltetrazol-5-yl)biphenyl (VI) with L-valine benzyl ester to produce N-[[2′-(1-triphenylmethyltetrazol-5-yl)biphenyl-4-yl]-methyl]-L-valine benzyl ester (VII), followed by treatment with valeryl chloride to produce N-(1-oxopentyl)-N-[[2′-(1-triphenylmethyltetrazol-5-yl)[1,1′-biphenyl]-4-yl]-methyl]-L-valine benzyl ester (VIII). Compound (VIII) is deprotected under acidic conditions to produce N-(1-oxopentyl)-N-[[2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]-methyl]-L-valine benzyl ester (IX), which is then hydrogenated in presence of Pd/C catalyst to give finally Valsartan. The process is shown in scheme II, below:

Sources & evidence

ORD record
ord-904d09ad5c084e2b95404db93c776664
Source dataset
uspto-grants-2011_02
Patent number
US07880015B2

Reaction notes

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