Hydrochloric Acid → 2-[4-(4-bromo-2-fluorophenylmethyl)-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetic acid

HRID 1655899Notes

Reaction equation

HRID 1655899 reaction equation
[OH-].[Na+].O1CCOCC1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[S:20][CH:19]([CH2:27][C:28]([O:30]CC)=[O:29])[C:18]2=[O:33])=[C:12]([F:34])[CH:11]=1.Cl>>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[S:20][CH:19]([CH2:27][C:28]([OH:30])=[O:29])[C:18]2=[O:33])=[C:12]([F:34])[CH:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10320899ethyl 2-[4-(4-bromo-2-fluorophenylmethyl)-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetateHCID 18323598NaOH dioxane

Product 1

HCID 100245272-[4-(4-bromo-2-fluorophenylmethyl)-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetic acidYield 94.6%

Procedure

To 8 ml of 1 N sodium hydroxide-dioxane (1:1) mixture was added 700 mg of the compound of Example 20. After the mixture had been stirred at room temperature for 2 hours, it was acidified with 1 N hydrochloric acid. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water dried, and concentrated. The resulting crude product was recrystallized from ethyl acetate-isopropyl ether to give 620 mg of 2-[4-(4-bromo-2-fluorophenylmethyl)-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetic acid. The structural formula and physical data of this compound are shown in Table 36.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting crude product was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-fbe7fa10197b4f3ca9239ad620d29219
Source dataset
uspto-grants-1993_10
Patent number
US05252571

Reaction notes

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