HCID 19818603, compound → HCID 178466798, compound

HRID 620314Notes

Reaction equation

HRID 620314 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, crystallization 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-94676370de154764a55464ac95bca9e1
Source dataset
uspto-grants-1989_04
Patent number
US04820726

Reaction notes

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