Losartan → Losartan potassium salt

HRID 1824570Notes

Reaction equation

HRID 1824570 reaction equation
[OH-].[K+:2].[CH3:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]3[N:29]=[N:28][NH:27][N:26]=3)=[CH:17][CH:18]=2)[C:10]([CH2:30][OH:31])=[C:9]([Cl:32])[N:8]=1>C(O)(C)C>[CH3:3][CH2:4][CH2:5][CH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]3[N:29]=[N:28][N-:27][N:26]=3)=[CH:15][CH:14]=2)[C:10]([CH2:30][OH:31])=[C:9]([Cl:32])[N:8]=1.[K+:2]

Participants

4

Reactant 2

HCID 3961LosartanHCID 14797Potassium Hydroxide

Product 1

HCID 11476710Losartan potassium saltYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of potassium hydroxide (9.4 g) and isopropyl alcohol (200 mL) was slowly added to a suspension of losartan (60 g) in isopropyl alcohol (280mL). The reaction mixture was stirred for about 2 hours at room temperature. The mixture was filtered, heated to reflux, concentrated to about a 180 mL volume and stirred for about 12 hours at room temperature. The precipitate was filtered, washed with isopropyl alcohol, and dried under reduced pressure for about 2 hours at about 50° C. to give losartan potassium (52.2 g, 85% yield) as a white powder. Purity was determined to be 99.74% by HPLC. Losartan potassium (1.0 g) was triturated with ethyl acetate (10 mL) and recovered from the triturate in a purity of 99.775% by HPLC.

Workup

  1. filtrationThe mixture was filtered
  2. temperatureheated
  3. temperatureto reflux
  4. concentrationconcentrated to about a 180 mL volume
  5. stirringstirred for about 12 hours at room temperature
  6. filtrationThe precipitate was filtered
  7. washwashed with isopropyl alcohol
  8. customdried under reduced pressure for about 2 hours at about 50° C.

Sources & evidence

ORD record
ord-4ee830e3ba7c4434a9001116ce5c6fb2
Source dataset
uspto-grants-2006_05
Patent number
US07041832B2

Reaction notes

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