Sodium Hydroxide → HCID 178521858, compound

HRID 2165088Notes

Reaction equation

HRID 2165088 reaction equation
[OH-].[Na+].C([O:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:37]=[CH:36][C:17]([C:18]([NH:20][C:21]2[C:26]3[O:27][CH:28]([C:31]4[NH:35][N:34]=[N:33][N:32]=4)[CH2:29][O:30][C:25]=3[CH:24]=[CH:23][CH:22]=2)=[O:19])=[CH:16][CH:15]=1)(=O)C>CO>[OH:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:20][C:21]2[C:26]3[O:27][CH:28]([C:31]4[NH:35][N:34]=[N:33][N:32]=4)[CH2:29][O:30][C:25]=3[CH:24]=[CH:23][CH:22]=2)=[O:19])=[CH:36][CH:37]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178476258HCID 178476258, compound

Product 1

HCID 178521858HCID 178521858, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1N aqueous solution of sodium hydroxide (0.5 ml) was added to a solution of 8-[p-(6-acetyloxyhexyloxy)benzoyl]amino-2-(5-tetrazolyl)-1,4-benzodioxane (100 mg; synthesized in example 1 (96)) in methanol (0.5 ml) at room temperature. The reaction solution was stirred for 10 min at the same temperature, and then concentrated under reduced pressure. To the residue, dil. hydrochloric acid was added and the mixture was extracted with ethyl acetate. The extract was dried and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (methylene chloride:methanol=100:1) to give the title compound (95 mg) having the following physical data:

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue, dil. hydrochloric acid was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe extract was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (methylene chloride:methanol=100:1)

Sources & evidence

ORD record
ord-41c55509cdc048a4a052a42210ec29ef
Source dataset
uspto-grants-1990_07
Patent number
US04939141

Reaction notes

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