Hydrochloric Acid → Irbesartan

HRID 1393197

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](=[O:37])[C:7]2([CH2:41][CH2:40][CH2:39][CH2:38]2)[N:6]=1)[CH2:2][CH2:3][CH3:4].Cl>C1(C)C=CC=CC=1>[CH3:4][CH2:3][CH2:2][CH2:1][C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:24]=[N:25][NH:26][N:27]=3)=[CH:15][CH:16]=2)[C:8](=[O:37])[C:7]2([CH2:38][CH2:39][CH2:40][CH2:41]2)[N:6]=1

Participants

Conditions

Temperature: 17.5 °C

Procedure

124 g (0.228 moles) of 2-butyl-3-{2′-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-biphenyl-4-ylmethyl}-1,3-diaza-spiro[4.4]non-1-en-4-one are dissolved in 500 ml of toluene and 900 ml of 37% aqueous hydrochloric acid are added thereto under stirring at a temperature of 15-20° C. The mixture is stirred for a further 4 h, then the aqueous phase is separated and washed twice with 250 ml of toluene. The aqueous phase is poured into a solution of 125 g of sodium acetate in water, the formed precipitate is filtered, thoroughly washed with water and dried under vacuum at 70° C., thereby obtaining 77 g of irbesartan.

Workup

stirringThe mixture is stirred for a further 4 h
customthe aqueous phase is separated
washwashed twice with 250 ml of toluene
additionThe aqueous phase is poured into a solution of 125 g of sodium acetate in water
filtrationthe formed precipitate is filtered
washthoroughly washed with water
customdried under vacuum at 70° C.

Sources & evidence

ORD record: ord-19a9f64464b1471596ae96d4df478891
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07345072B2

Linked notes

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