Ethanol → N-[[2'-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]valine methyl ester

HRID 1362769Notes

Reaction equation

HRID 1362769 reaction equation
[CH3:1][O:2][C:3](=[O:46])[C@H:4]([CH:43]([CH3:45])[CH3:44])[NH:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[N:23]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:22]=[N:21][N:20]=2)=[CH:9][CH:8]=1.[C:47]([OH:52])(=[O:51])[C:48]([OH:50])=[O:49].O.O.C(O)(=O)C(O)=O.C(O)C>C(OCC)(=O)C.C(Cl)Cl.C(O)C(C)C.C(O)CCC.C(O)(C)C.C(O)CC>[CH3:1][O:2][C:3](=[O:46])[C@H:4]([CH:43]([CH3:44])[CH3:45])[NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[N:23]([C:24]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:22]=[N:21][N:20]=2)=[CH:11][CH:12]=1.[C:47]([OH:52])(=[O:51])[C:48]([OH:50])=[O:49].[CH3:1][O:2][C:3](=[O:46])[C@H:4]([CH:43]([CH3:44])[CH3:45])[NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]2[N:23]([C:24]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:22]=[N:21][N:20]=2)=[CH:11][CH:12]=1

Participants

12

Reactant 4

HCID 702EthanolHCID 971Oxalic AcidHCID 61373Oxalic acid dihydrateHCID 11399301N-[[2'-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]valine methyl ester

Product 2

HCID 11399301N-[[2'-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]valine methyl esterHCID 23725720N-[[2'-(1-triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]valine methyl ester oxalate

Reagents, catalysts & solvents 6

HCID 2631-ButanolSolventHCID 10311-PropanolSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 6560IsobutanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[[2′-(1-Triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]valine methyl ester (X) is prepared according to the process described in U.S. Pat. No. 5,399,578. N-[[2′-(1-triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]valine methyl ester (X) is reacted with a molar equivalent of oxalic acid or its hydrates selected from oxalic acid dihydrate in an organic solvent selected from alcohols such as ethanol, n-propanol, isopropanol, n-butanol, isobutanol, methylene chloride, ethyl acetate or mixtures thereof, at a temperature of about −20° C. to about 70° C. and the product obtained is isolated by filtration and dried. The product obtained is purified in a solvent selected from chlorinated hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, preferably methylene chloride to produce N-[[2′-(1-triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]valine methyl ester oxalate (Xa) in crystalline form. It has been observed that preparation of oxalic acid salt of Formula (X) results in greater than 98% purity of product by HPLC analysis.

Workup

  1. customat a temperature of about −20° C. to about 70° C. and the product obtained
  2. customis isolated by filtration
  3. customdried
  4. customThe product obtained
  5. customis purified in a solvent

Sources & evidence

ORD record
ord-f0c91159fd7f419f9b1c4b6f0def4e40
Source dataset
uspto-grants-2011_02
Patent number
US07880015B2

Reaction notes

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