Ethyl Acetate → HCID 19036212, compound

HRID 52909Notes

Reaction equation

HRID 52909 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([O:13][CH2:14]Cl)(=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9].[OH:16][CH2:17][C:18]1[N:19]=[C:20]([CH2:63][CH2:64][CH3:65])[N:21]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[N:43]([C:44]([C:57]4[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=4)([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:42]=[N:41][N:40]=3)=[CH:29][CH:28]=2)[C:22]=1[C:23]([OH:25])=[O:24].C(OCC)(=O)C>CN(C)C(=O)C.O>[OH:16][CH2:17][C:18]1[N:19]=[C:20]([CH2:63][CH2:64][CH3:65])[N:21]([CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[C:39]3[N:43]([C:44]([C:51]4[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=4)([C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[N:42]=[N:41][N:40]=3)=[CH:31][CH:32]=2)[C:22]=1[C:23]([O:25][CH2:14][O:13][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])=[O:24]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 190361844-Hydroxymethyl-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylic acid

Product 1

HCID 19036212HCID 19036212, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Procedure

0.30 g of potassium carbonate and 0.24 g of pivaloyloxymethyl chloride were added to a solution of 0.98 g of 4-hydroxymethyl-2-propyl-1-{4-[2-(trityltetrazol-5-yl)phenyl]phenyl}methylimidazole-5-carboxylic acid [prepared as described in step (a) above] in 10 ml of N,N-dimethylacetamide, and the resulting mixture was stirred at room temperature for 6 hours. At the end of this time, the reaction mixture was mixed with ethyl acetate and water. The ethyl acetate layer was separated and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 2:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 0.91 g of the title compound as a gum.

Workup

  1. customThe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed by distillation under reduced pressure
  4. customThe resulting residue was purified by column chromatography through silica gel
  5. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-71cd08426c774964968b779b4de4ba99
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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