Water → HCID 19936830, compound

HRID 2081851Notes

Reaction equation

HRID 2081851 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[C:7]([CH:10]([OH:23])[C:11](C)([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[C:32](OC(=O)C)(=[O:34])[CH3:33].O>CN(C)C1C=CN=CC=1.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[C:32]([O:23][CH:10]([C:7]1[N:6]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][CH:8]=1)[CH:11]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[C:12]([O:14][CH3:15])=[O:13])(=[O:34])[CH3:33]

Participants

7

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 67885272HCID 67885272, compound

Product 1

HCID 19936830HCID 19936830, compoundYield 113.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of methyl 3-[2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-yl]-3-hydroxy-2-(4-pyridyl)-methylpropanoate (3.32 g, 7.5 mmol) methylene chloride (50 mL), 4-dimethylaminopyridine (150 mg, 1.3 mmol) and acetic anhydride (7.1 mL, 75 mmol) was stirred at ambient temperature for 18 hours. Water (5 mL) was added, the mixture was stirred for 2 hours and then diluted with methylene chloride and 5% sodium bicarbonate solution. The organic phase was washed with 5% sodium bicarbonate solution and brine, dried and concentrated to give 4 g of the crude title compound. TLC on silica gel with 5% methanol ethyl acetate showed essentially one spot material with an Rf of 0.86. No starting material was detected. This material was not purified further.

Workup

  1. washThe organic phase was washed with 5% sodium bicarbonate solution and brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-71512f6e827d4d58b315c4dfed05f71f
Source dataset
uspto-grants-1993_02
Patent number
US05185351

Reaction notes

Loading…