Valeryl chloride → HCID 57823153, compound

HRID 453950Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:15])[C@H:10]([CH:12]([CH3:14])[CH3:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](Cl)(=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20]>>[CH2:1]([O:8][C:9](=[O:15])[C@H:10]([CH:12]([CH3:13])[CH3:14])[NH:11][C:16](=[O:21])[CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 61186Valeryl chloride

HCID 6950584benzyl (2S)-2-amino-3-methylbutanoate

Product 1

HCID 57823153HCID 57823153, compound

Procedure

According to EP 1714963 4-Bromomethyl-2′-cyanobiphenyl is condensed with L-valinebenzylester tosylate to give (S)-N-[(2′-cyanobiphenyl-4-yl]methyl]-(L)-valine benzylester hydrochloride. (S)-N-cyanobiphenyl-4-yl]methyl]-(L)-valine benzylester on reaction with valerylchloride yields (S)-N-cyanobiphenyl-4-yl]methyl]-N-valeryl-(L)-valine benzylester further by the reaction of tributyltin chloride and sodiumazide gives benzyl valsartan and debenzylation with Pd/C to give valsartan. Also discloses the process for the recovery of benzyl valsartan substantially free of organo tin impurity.

Sources & evidence

ORD record: ord-f897accd59864cd0b0d8f47a866dca81
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492577B2

Reaction notes

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