Losartan → Losartan potassium salt

HRID 1824569Notes

Reaction equation

HRID 1824569 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 86.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A solution of potassium hydroxide (0.305 g, 4.62 mmol (1 eq.)) and isopropyl alcohol (15 mL) was slowly added to a suspension of losartan (2.0 g, 4.73 mmol) in isopropyl alcohol (25 mL). The reaction mixture was stirred for about 2 hours at room temperature. The mixture was filtered, concentrated to about a 15 mL volume, heated to reflux and stirred for about 12 hours at room temperature. The precipitate was filtered, washed with isopropyl alcohol (5 mL), and dried under reduced pressure for about 2 hours at about 50° C. to give losartan potassium (1.85 g, 85% yield) as a white powder. Purity was determined to be 99.74% by HPLC. Losartan potassium (1.0 g) was then 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. concentrationconcentrated to about a 15 mL volume
  3. temperatureheated
  4. temperatureto reflux
  5. stirringstirred for about 12 hours at room temperature
  6. filtrationThe precipitate was filtered
  7. washwashed with isopropyl alcohol (5 mL)
  8. customdried under reduced pressure for about 2 hours at about 50° C.

Sources & evidence

ORD record
ord-4c4665bcaf8d4fe28aa29c5c3b63ae27
Source dataset
uspto-grants-2006_05
Patent number
US07041832B2

Reaction notes

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