Hydrochloric Acid → HCID 178443724, compound

HRID 231568Notes

Reaction equation

HRID 231568 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:13][CH2:12][CH:11]([C:14]3[NH:18][N:17]=[N:16][N:15]=3)[O:10][C:9]=2[C:19]=1[NH:20][C:21](=[O:37])[C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[CH:24][CH:23]=1)=[O:4].[OH-].[Na+].Cl>CO>[CH2:29]([O:28][C:25]1[CH:26]=[CH:27][C:22]([C:21]([NH:20][C:19]2[C:9]3[O:10][CH:11]([C:14]4[NH:18][N:17]=[N:16][N:15]=4)[CH2:12][O:13][C:8]=3[CH:7]=[CH:6][C:5]=2[C:3]([OH:4])=[O:2])=[O:37])=[CH:23][CH:24]=1)[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178443725HCID 178443725, compound

Product 1

HCID 178443724HCID 178443724, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-(p-octyloxybenzoyl)amino-2-(5-tetrazolyl)-1,4-benzodioxane-7-carboxylic acid methyl ester (332 mg; synthesized in example 2 (107) was dissolved in methanol (1.5 ml). To the solution, a 1N aqueous solution of sodium hydroxide (1.36 ml), and the mixture was stirred for 50 min at room temperature and for 2 hrs at 40° C. After cooling, 1N hydrochloric acid (2 ml) was added to the solution. 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 (chloroform: methanol=9:1) to give the title compound (263 mg) having the following physical data:

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe extract was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (chloroform: methanol=9:1)

Sources & evidence

ORD record
ord-4b5355fdf97541048c7b7f6ae16fef4b
Source dataset
uspto-grants-1989_07
Patent number
US04847275

Reaction notes

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