Lithium Hydroxide → [3-(4-Benzenesulfonylthiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid

HRID 1944483Notes

Reaction equation

HRID 1944483 reaction equation
[OH-].[Li+].O1CCCC1.C[O:9][C:10](=[O:38])[CH2:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=2)[C:14]([CH2:22][C:23]2[S:27][CH:26]=[N:25][C:24]=2[S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])=[C:13]1[CH3:37]>O>[C:31]1([S:28]([C:24]2[N:25]=[CH:26][S:27][C:23]=2[CH2:22][C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)[N:12]([CH2:11][C:10]([OH:38])=[O:9])[C:13]=2[CH3:37])(=[O:29])=[O:30])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67044096[3-(4-Benzenesulfonylthiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester

Product 1

HCID 42645097[3-(4-Benzenesulfonylthiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of lithium hydroxide (0.10 g), tetrahydrofuran (1.0 mL) and water (1.0 mL) was treated [3-(4-benzenesulfonylthiazol-5-ylmethyl)-5-fluoro-2-methylindol-1-yl]acetic acid methyl ester (0.20 g), and the resulting mixture was stirred at room temperature for 30 minutes. The mixture was diluted with water, concentrated to low bulk under reduced pressure and acidified by the addition of 1.0 M aqueous hydrochloric acid solution. The resulting precipitate was collected by filtration, washed with water and dried to afford the title compound as a white solid (0.19 g).

Workup

  1. concentrationconcentrated to low bulk under reduced pressure
  2. additionacidified by the addition of 1.0 M aqueous hydrochloric acid solution
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f8fad8f3feca4572bfc7a4ca7b0a1e2c
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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