HCID 15718333, compound → HCID 178439719, compound

HRID 1382815Notes

Reaction equation

HRID 1382815 reaction equation
[C:1]([C:4]1[CH:40]=[CH:39][C:7]([O:8][CH2:9][CH:10]([OH:38])[CH2:11][O:12][C:13]2[C:14]([C:36]#[N:37])=[C:15]([NH:19][C:20]([C:22]3[N:26](CC4C=CC(OC)=CC=4)[N:25]=[N:24][N:23]=3)=[O:21])[CH:16]=[CH:17][CH:18]=2)=[C:6]([CH2:41][CH2:42][CH3:43])[C:5]=1[OH:44])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[C:1]([C:4]1[CH:40]=[CH:39][C:7]([O:8][CH2:9][CH:10]([OH:38])[CH2:11][O:12][C:13]2[C:14]([C:36]#[N:37])=[C:15]([NH:19][C:20]([C:22]3[NH:26][N:25]=[N:24][N:23]=3)=[O:21])[CH:16]=[CH:17][CH:18]=2)=[C:6]([CH2:41][CH2:42][CH3:43])[C:5]=1[OH:44])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 15718333HCID 15718333, compound

Product 1

HCID 178439719HCID 178439719, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of 7.1 g (11.8 mmol) of N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-2-hydroxypropoxy]-2-cyanophenyl}-1-(4-methoxybenzyl)tetrazole-5-carboxamide in 150 ml of trifluoroacetic acid and 15 ml of anisole is heated at reflux temperature for 30 minutes. The reaction mixture is concentrated under reduced pressure, about 200 ml of ether and 300 ml of petroleum ether are added to the residue, and the crystals are filtered off. The N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-2-hydroxypropoxy]-2-cyanophenyl}-1H-tetrazole-5-carboxamide of melting point 210°-213° thus obtained is dissolved in 50 ml of hot acetone, and one equivalent of triethanolamine in 20 ml of acetone is added. Crystallisation sets in after ether has been addded. This gives the triethanolammonium salt of N-{3-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-2-hydroxypropoxy]-2-cyanophenyl}-1H-tetrazole-5-carboxamide of melting point 80°-82°.

Workup

  1. temperatureat reflux temperature for 30 minutes
  2. concentrationThe reaction mixture is concentrated under reduced pressure, about 200 ml of ether and 300 ml of petroleum ether
  3. additionare added to the residue
  4. filtrationthe crystals are filtered off

Sources & evidence

ORD record
ord-ae2968378bff449cbc60d00a75e8b80a
Source dataset
uspto-grants-1989_02
Patent number
US04808604

Reaction notes

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