HCID 23464494, compound → HCID 13013942, compound

HRID 444159Notes

Reaction equation

HRID 444159 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6](=[O:14])(=[O:13])[C:5]2[CH:15]=[C:16]([C:19]([O:21]C)=[O:20])[CH:17]=[CH:18][C:4]=2[NH:3]1>[OH-].[Na+].O1CCCC1>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6](=[O:14])(=[O:13])[C:5]2[CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=[CH:18][C:4]=2[NH:3]1

Participants

4

Reactant 1

HCID 23464494HCID 23464494, compound

Product 1

HCID 13013942HCID 13013942, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Stir at room temperature 795 mg of the ester of Example 26 in a mixture of 50 ml of 10% aqueous sodium hydroxide and 50 ml of tetrahydrofuran for 3 hours. Separate the layers and extract the organic layer with 10% aqueous sodium hydroxide. Wash the combined aqueous layers with ether and acidify with acetic acid. Separate the precipitate by filtration, wash with water and dry in order to obtain the title product (m.p. 337°-340° C. with subsequent dec.).

Workup

  1. customSeparate the layers
  2. extractionextract the organic layer with 10% aqueous sodium hydroxide
  3. washWash the combined aqueous layers with ether
  4. customSeparate the precipitate
  5. filtrationby filtration
  6. washwash with water
  7. customdry in order

Sources & evidence

ORD record
ord-5b0db2b8752b4bfda8651098d43fa9ab
Source dataset
uspto-grants-1981_04
Patent number
US04263207

Reaction notes

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