Acetonitrile → HCID 86758192, compound

HRID 1370618Notes

Reaction equation

HRID 1370618 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:35])([CH2:29][N:30]1[CH:34]=[N:33][CH:32]=[N:31]1)[C@H:10]([N:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH:27]=[CH:26][N:25]=[N:24]3)=[CH:19][CH:18]=2)[C:13]1=[O:28])[CH3:11].[C:36](=[O:44])([O:41][CH2:42][CH3:43])[O:37][CH:38]([Cl:40])[CH3:39].C(#N)C>C(OC(C)C)(C)C>[Cl-:40].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]([OH:35])([C@H:10]([N:12]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([N:23]3[CH:27]=[CH:26][N:25]=[N:24]3)=[CH:21][CH:22]=2)[C:13]1=[O:28])[CH3:11])[CH2:29][NH+:30]1[CH2:34][N:33]([CH:38]([O:37][C:36]([O:41][CH2:42][CH3:43])=[O:44])[CH3:39])[CH:32]=[N:31]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 162095Carbonic acid, 1-chloroethyl ethyl esterHCID 3002971HCID 3002971, compound

Product 1

HCID 86758192HCID 86758192, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]-3-[4-(1H-1,2,3-triazol-1-yl)phenyl]-2-imidazolidinone (100 mg) and 1-chloroethyl ethyl carbonate (1.0 g) was added acetonitrile (0.5 ml), and the mixture was stirred for 60 hours at 85° C. After having been cooled, the mixture was diluted with diisopropyl ether (4 ml), and the resulting powder was collected by filtration. The powder was subjected to ODS column chromatography (eluent: methanol/water=3/2). The eluate was concentrated in vacuo. The residue was dissolved in water (10 ml) and lyophilized to give 1-[(2R,3R)-2-(2,4-difluorophenyl)-2-hydroxy-3-[2-oxo-3-[4-(1H-1,2,3-triazol-1-yl)phenyl]-1-imidazolidinyl]butyl]-4-[1-(ethoxycarbonyloxy)ethyl]-1H-1,2,4-triazolium chloride(Compound 6, 36 mg) as a white powder.

Workup

  1. temperatureAfter having been cooled
  2. filtrationthe resulting powder was collected by filtration
  3. concentrationThe eluate was concentrated in vacuo
  4. dissolutionThe residue was dissolved in water (10 ml)

Sources & evidence

ORD record
ord-63d4e71f34d542919e09c8af8a9f560c
Source dataset
uspto-grants-2003_06
Patent number
US06583164B1

Reaction notes

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