Water → HCID 19936830, compound

HRID 36986Notes

Reaction equation

HRID 36986 reaction equation
[CH2:1]([C:5]1[N:6]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2Cl)[C:7]([CH:11]([OH:24])[C:12](C)([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[C:13]([O:15][CH3:16])=[O:14])=[C:8](C)[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:32](OC(=O)C)(=[O:34])[CH3:33].O.[CH2:40]([Cl:42])Cl>CN(C)C1C=CN=CC=1.C(=O)(O)[O-].[Na+]>[C:32]([O:24][CH:11]([C:7]1[N:6]([CH2:25][C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:40]=2[Cl:42])[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:9][CH:8]=1)[CH:12]([C:17]1[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:34])[CH3:33]

Participants

7

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 69948568methyl 3-[2-n-butyl-1-(2-chlorophenyl)-methyl-1H-imidazol-5-yl]-3-hydroxy-2-(4-pyridyl)-methylpropanoate

Product 1

HCID 19936830HCID 19936830, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 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-afc794352bd647998ba217e408ddf4b8
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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