3-(1H-tetrazol-1-yl)benzoic acid → 3-Oxo-3-(3-tetrazol-1-yl-phenyl)-propionic acid ethyl ester

HRID 1635234Notes

Reaction equation

HRID 1635234 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([OH:11])=O)[CH:5]=[N:4][N:3]=[N:2]1.ClC(OCC)=O.CCN(CC)CC.[K+].[C:29]([O:35][CH2:36][CH3:37])(=[O:34])[CH2:30]C([O-])=O.[Mg+2].[Cl-].[Cl-]>CC#N.CCN(CC)CC>[CH2:36]([O:35][C:29](=[O:34])[CH2:30][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([N:1]2[CH:5]=[N:4][N:3]=[N:2]2)[CH:7]=1)[CH3:37]

Participants

7

Reactant 4

HCID 7502203-(1H-tetrazol-1-yl)benzoic acidHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium ChlorideHCID 19692316ethyl chloroformate Et3N

Product 1

HCID 695927913-Oxo-3-(3-tetrazol-1-yl-phenyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Prepared from 3-tetrazol-1-yl-benzoic acid [CAS-No. 204196-80-5] by activation with ethyl chloroformate/Et3N and reaction with ethyl malonate potassium salt with Et3N and MgCl2 in CH3CN according to general procedure H (method a). Obtained as a light yellow solid (211 mg).

Sources & evidence

ORD record
ord-09672bdefe2b4d249beff72eb87b61e1
Source dataset
uspto-grants-2003_01
Patent number
US06509328B1

Reaction notes

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