Acetic Acid → HCID 178441607, compound

HRID 1648524Notes

Reaction equation

HRID 1648524 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[N:27](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:26]=[N:25][N:24]=3)=[CH:13][CH:12]=2)[C:8]([CH:47]=[C:48]2[N:52]([CH3:53])[C:51](=[O:54])[NH:50][C:49]2=[O:55])=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4].CO.C(O)(=O)C>O>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23]3[NH:27][N:26]=[N:25][N:24]=3)=[CH:15][CH:16]=2)[C:8](/[CH:47]=[C:48]2\[C:49](=[O:55])[NH:50][C:51](=[O:54])[N:52]\2[CH3:53])=[CH:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 54450286HCID 54450286, compound

Product 1

HCID 178441607HCID 178441607, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of the E and Z-isomers of 5-[[2-butyl-3-[[2'-(N-triphenylmethyl-tetrazol-5-yl) [1,1'-biphenyl]-4-yl]methyl]-3H-imidazol-4-yl]methylene]-1-methyl-2,4-imidazolidinedione (0.400 g, 0.552 mmol ) was added methanol (50 mL) and glacial acetic acid (0.2 mL). This white heterogeneous mixture was refluxed for 3 hour in which time a solution formed. The solution was cooled to room temperature and diluted with water (5 mL) and hexanes (50 mL). The aqueous methanol fraction was evaporated in vacuo and then triturated with ethyl acetate. The insoluble residue was collected and determined to be the E-isomer. HPLC eluant 45%(0.1%TFA in H2O) 55% MeCN, RT 1.9[95%] MS (CI) 483 (M+1)

Workup

  1. temperatureThis white heterogeneous mixture was refluxed for 3 hour in which time a solution
  2. customformed
  3. customThe aqueous methanol fraction was evaporated in vacuo
  4. customtriturated with ethyl acetate
  5. customThe insoluble residue was collected
  6. customHPLC eluant 45%(0.1%TFA in H2O) 55% MeCN, RT 1.9[95%]

Sources & evidence

ORD record
ord-e11d8733d88f4da599a5a370f48c30b4
Source dataset
uspto-grants-1995_07
Patent number
US05436260

Reaction notes

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