Water → Ethyl 4-(1-hydroxy-1-methylethyl)-2-methylthiomethyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

HRID 53011Notes

Reaction equation

HRID 53011 reaction equation
[CH3:1][S-:2].[Na+].[OH:4][C:5]([C:8]1[N:9]=[C:10]([CH2:55]OS(C)(=O)=O)[N:11]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[N:35]([C:36]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[N:34]=[N:33][N:32]=3)=[CH:21][CH:20]=2)C=1C(OCC)=O)([CH3:7])[CH3:6].[C:61]([O:64][CH2:65][CH3:66])(=[O:63])[CH3:62].O>CN(C)C=O>[OH:4][C:5]([C:8]1[N:9]=[C:10]([CH2:55][S:2][CH3:1])[N:11]([CH2:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]3[N:35]([C:36]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[N:34]=[N:33][N:32]=3)=[CH:23][CH:24]=2)[C:62]=1[C:61]([O:64][CH2:65][CH3:66])=[O:63])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4378561Sodium methanethiolateHCID 19036237HCID 19036237, compound

Product 1

HCID 19036273Ethyl 4-(1-hydroxy-1-methylethyl)-2-methylthiomethyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50.3 ml of sodium methanethiolate were added to a solution of 610 mg of ethyl 4-(1-hydroxy-1-methylethyl)-2-methanesulfonyloxymethyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylate [prepared as described in step (c) above] in 6 ml of N,N-dimethylformamide. The mixture was stirred at room temperature for 45 minutes, after which it was mixed with ethyl acetate and water. The ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and then concentrated by evaporation under reduced pressure, after which the residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and ethyl acetate as the eluent, to give 338 mg of the title compound as crystals, melting at 174.5°-176.5° C. (with decomposition).

Workup

  1. customThe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customafter which the residue was purified by column chromatography through silica gel
  5. additionby volume mixture of methylene chloride and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-41e6f81f715c4017b0ab7df7a091cea0
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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