Losartan Cum-Alcohol → Losartan

HRID 1393194Notes

Reaction equation

HRID 1393194 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]>Cl>[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 94.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
17.5 °C

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 37% aqueous hydrochloric acid under stirring at a temperature of 15-20° C. The mixture is stirred for a further 4 h, then washed 3 times with 25 ml of toluene. The aqueous phase 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 8 g of losartan.

Workup

  1. stirringThe mixture is stirred for a further 4 h
  2. washwashed 3 times with 25 ml of toluene
  3. additionThe aqueous phase is poured into a solution of 55 g of sodium acetate in water
  4. filtrationthe formed precipitate is filtered
  5. washthoroughly washed with water
  6. customdried under vacuum at 70° C.

Sources & evidence

ORD record
ord-38fed129728b49d8be21dba49c4e837d
Source dataset
uspto-grants-2008_03
Patent number
US07345072B2

Reaction notes

Loading…