Losartan Cum-Alcohol → Losartan

HRID 1393195Notes

Reaction equation

HRID 1393195 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:24]=[N:25][N:26](C(C)(C4C=CC=CC=4)C)[N:27]=3)=[CH:13][CH:12]=2)[C:8]([CH2:37][OH:38])=[C:7]([Cl:39])[N:6]=1)[CH2:2][CH2:3][CH3:4]>ClCCl>[CH3:4][CH2:3][CH2:2][CH2:1][C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:27]=[N:26][NH:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]([CH2:37][OH:38])=[C:7]([Cl:39])[N:6]=1

Participants

3

Reactant 1

HCID 11387152Losartan Cum-Alcohol

Product 1

HCID 3961LosartanYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g (0.02 moles) of (2-butyl-5-chloro-3-{2′-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-3H-imidazol-4-yl)-methanol are dissolved in 50 ml of dichloromethane and gaseous HCl is bubbled at a temperature of 0-10° C. After 2 h the reaction mixture is poured into a solution of 55 g of sodium acetate in water, the formed precipitate is filtered, thoroughly washed with water and dried under vacuum at 70° C., thereby obtaining 7.8 g of losartan.

Workup

  1. customgaseous HCl is bubbled at a temperature of 0-10° C
  2. additionAfter 2 h the reaction mixture is poured into a solution of 55 g of sodium acetate in water
  3. filtrationthe formed precipitate is filtered
  4. washthoroughly washed with water
  5. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-29fe4c234bb541edb7482195f09998df
Source dataset
uspto-grants-2008_03
Patent number
US07345072B2

Reaction notes

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