Hydrochloric Acid → (-)-4-[2-(Hydroxyamino)-2-oxoethyl]-2-[3-(4-methoxyphenyl)propyl]-3-oxo-3,4-dihydro-2h-1,4-benzothiazine-6-carboxylic acid

HRID 1817189Notes

Reaction equation

HRID 1817189 reaction equation
[OH:1][NH:2][C:3](=[O:32])[CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([C:15]([O:17]CC)=[O:16])[CH:13]=[CH:14][C:9]=2[S:8][CH:7]([CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:6]1=[O:31].C1COCC1.[OH-].[Li+].Cl>C(OCC)(=O)C.O>[OH:1][NH:2][C:3](=[O:32])[CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=[CH:14][C:9]=2[S:8][CH:7]([CH2:20][CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)[C:6]1=[O:31]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 23157964Ethyl 4-[2-(hydroxyamino)-2-oxoethyl]-2-[3-(4-methoxyphenyl)propyl]-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate

Product 1

HCID 23157951(-)-4-[2-(Hydroxyamino)-2-oxoethyl]-2-[3-(4-methoxyphenyl)propyl]-3-oxo-3,4-dihydro-2h-1,4-benzothiazine-6-carboxylic acidYield 67.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the compound of Example 1 (0.51 g) were added THF (10 ml) and water (10 ml). After the resulting mixture was ice-cooled, a 0.5N aqueous lithium hydroxide solution (4.4 ml) was slowly added dropwise thereto. The resulting mixture was slowly warmed up to room temperature and stirred overnight. Ice-cooled 1N aqueous hydrochloric acid solution and ethyl acetate were added thereto to effect extraction. The oil layer was washed twice with a 1N aqueous hydrochloric acid solution, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. Chloroform was added to the residue, and after standing for 4 days, the solid precipitated was collected by filtration and dried under reduced pressure. 4-[2-(Hydroxyamino)-2-oxoethyl]-2-[3-(4-methoxyphenyl)propyl]-3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid (325 mg) was obtained as a white solid.

Workup

  1. temperaturecooled
  2. additionwere added
  3. extractionextraction
  4. washThe oil layer was washed twice with a 1N aqueous hydrochloric acid solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionChloroform was added to the residue
  8. waitafter standing for 4 days
  9. customthe solid precipitated
  10. filtrationwas collected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-dddfc9f2bcb949ca8d60e3b642be9e6e
Source dataset
uspto-grants-2009_10
Patent number
US07598240B2

Reaction notes

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