HCID 19818603, compound → HCID 178466798, compound

HRID 1086936Notes

Reaction equation

HRID 1086936 reaction equation
[C:1]([C:4]1[CH:38]=[CH:37][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([NH:20][C:21]([C:23]3[N:27](CC4C=CC(OC)=CC=4)[N:26]=[N:25][N:24]=3)=[O:22])[C:16]([CH3:19])=[CH:17][CH:18]=2)=[C:6]([CH2:39][CH2:40][C:41]([F:44])([F:43])[F:42])[C:5]=1[OH:45])(=[O:3])[CH3:2]>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>[C:1]([C:4]1[CH:38]=[CH:37][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]([NH:20][C:21]([C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[O:22])[C:16]([CH3:19])=[CH:17][CH:18]=2)=[C:6]([CH2:39][CH2:40][C:41]([F:42])([F:44])[F:43])[C:5]=1[OH:45])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 19818603HCID 19818603, compound

Product 1

HCID 178466798HCID 178466798, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of 2.84 g (4.5 mmol) of N-{{3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-6-methyl-phenyl}}-1-(4-methoxybenzyl)-tetrazole-5-carboxamide in 90 ml of trifluoroacetic acid and 9 ml of anisole is refluxed for 60 minutes. The reaction mixture is concentrated under reduced pressure, about 150 ml of ether and 300 ml of petroleum ether are added and the crystals are filtered off. The N-{{3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-6-methyl-phenyl}}-1H-tetrazole-5-carboxamide thus obtained, of melting point 236°-238° C. (decomposition), is dissolved in 50 ml of tetrahydrofuran, and one equivalent of sodium, dissolved in 5 ml of methanol, is added. After addition of ether, crystallizations starts. The sodium salt of N-{{3-{3-[4-acetyl-3-hydroxy-2-(3,3,3-trifluoropropyl)-phenoxy]-propoxy}-6-methyl-phenyl}}-1H-tetrazole-5-carboxamide of melting point 115°-125° C. (decomposition) is thus obtained.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, about 150 ml of ether and 300 ml of petroleum ether
  2. additionare added
  3. filtrationthe crystals are filtered off

Sources & evidence

ORD record
ord-e8db2378b5c34b1f91a2ba1fc1417a2c
Source dataset
uspto-grants-1991_07
Patent number
US05032606

Reaction notes

Loading…