Sodium Hydroxide → 2-[4-(5-fluorobenzothiazol-2-yl]methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetic acid

HRID 1655898Notes

Reaction equation

HRID 1655898 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[S:14][CH:13]([CH2:21][C:22]([O:24]CC)=[O:23])[C:12]3=[O:27])=[N:7][C:6]=2[CH:28]=1.[OH-].[Na+]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][N:11]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[S:14][CH:13]([CH2:21][C:22]([OH:24])=[O:23])[C:12]3=[O:27])=[N:7][C:6]=2[CH:28]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 9909828Ethyl 2-[4-(5-fluorobenzothiazol-2-yl)methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetate

Product 1

HCID 117409862-[4-(5-fluorobenzothiazol-2-yl]methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetic acidYield 76.4%

Procedure

The compound of Example 1 (275 mg) was dissolved in methanol-dioxane (1:2, v/v, 3 ml), and 0.7 ml of 2N sodium hydroxide solution was added dropwise to the solution with stirring at room temperature. The mixture was stirred for further 90 minutes. The solvent was distilled off and the residue was diluted with water, then the aqueous mixture was acidified with 10% hydrochloric acid. The precipitated solid was crystallized from chloroform-hexane to give 196 mg of the title compound. The structural formula and physical data of this compound are shown in Table 25.

Workup

  1. stirringThe mixture was stirred for further 90 minutes
  2. distillationThe solvent was distilled off
  3. additionthe residue was diluted with water
  4. customThe precipitated solid was crystallized from chloroform-hexane

Sources & evidence

ORD record
ord-be83ef69fa294685a6111271de31bf90
Source dataset
uspto-grants-1993_10
Patent number
US05252571

Reaction notes

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