Potassium Carbonate → Trityllosartan

HRID 654332Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[N:16]=[N:17][N:18]([C:20]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:19]=2)=[CH:5][CH:4]=1.[CH2:39]([C:43]1[NH:44][C:45]([CH:49]=[O:50])=[C:46]([Cl:48])[N:47]=1)[CH2:40][CH2:41][CH3:42].C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+]>CN(C)C(=O)C>[CH2:39]([C:43]1[N:44]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:15]3[N:16]=[N:17][N:18]([C:20]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[N:19]=3)=[CH:5][CH:4]=2)[C:45]([CH2:49][OH:50])=[C:46]([Cl:48])[N:47]=1)[CH2:40][CH2:41][CH3:42]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 5-(4'-bromomethyl-1,1'-biphenyl-2-yl)-2triphenylmethyl-2H-tetrazole (0.102 m=63.1 g), 2-n-butyl-4-chloro-1H-imidazole-5-carboxaldehyde (0.113 m=21.1 g) and anhydrous potassium carbonate (0.135 m=18.6 g) in 251 g of N,N-dimethylacetamide was stirred at 0°-5° C. for 8 hours and the temperature of the reaction was raised to 25° C. for an additional 4 hours. Normally the product of this step was not isolated but reduced with sodium borohydride to give 2-n-butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-methanol. The title compound can be isolated by extraction into toluene from aqueous N,N-dimethylacetamide, concentration of the toluene solution, and crystallization from ethyl acetate or ethanol, mp 145°-147° C. (dec.).

Workup

customNormally the product of this step was not isolated

Sources & evidence

ORD record: ord-d3356e5e8bc54490898b5f1a8741be2c
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05130439

Reaction notes

Loading…