Ammonium Chloride → HCID 70874438, compound

HRID 2172275Notes

Reaction equation

Cl[C:2]1[N:3]([CH2:10][CH2:11][C@@H:12]([OH:25])[CH2:13][O:14]S(C2C=CC(C)=CC=2)(=O)=O)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.O[C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][C:36]([C:40]3[CH:45]=[CH:44][C:43]([C:46]([F:49])([F:48])[F:47])=[CH:42][CH:41]=3)([OH:39])[CH2:35][CH2:34]2)=[CH:29][CH:28]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>C(O)C>[N+:7]([C:5]1[N:6]=[C:2]2[N:3]([CH:4]=1)[CH2:10][CH2:11][C@H:12]([CH2:13][O:14][C:27]1[CH:28]=[CH:29][C:30]([N:33]3[CH2:38][CH2:37][C:36]([C:40]4[CH:41]=[CH:42][C:43]([C:46]([F:48])([F:47])[F:49])=[CH:44][CH:45]=4)([OH:39])[CH2:35][CH2:34]3)=[CH:31][CH:32]=1)[O:25]2)([O-:9])=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of toluene-4-sulfonic acid (R)-4-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxybutyl ester (1.16 g), 1-(4-hydroxyphenyl)-4-(4-trifluoromethylphenyl)piperidin-4-ol (1.0 g), tripotassium phosphate (2.52 g) in ethanol (10 ml) was stirred at 60° C. for 15 hours under an argon atmosphere. The reaction mixture was added to an ammonium chloride aqueous solution, and the mixture was stirred for a while. The precipitated crude crystal was collected by filtration and dried at 60° C. The crude product thus obtained was purified by silica gel column chromatography (methylene chloride:ethyl acetate=1:1) and recrystallized from acetone-water to afford the title compound as a beige powder (0.63 g).

Workup

stirringthe mixture was stirred for a while
customThe precipitated crude crystal
filtrationwas collected by filtration
customdried at 60° C
customThe crude product thus obtained
customwas purified by silica gel column chromatography (methylene chloride:ethyl acetate=1:1)
customrecrystallized from acetone-water

Sources & evidence

ORD record: ord-d83583073cec48f7ae40d7e35272299b
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051333B2

Reaction notes

Loading…