Water → 3-(4-Chlorophenoxy)-2-methyl-4-[(methylsulfonyl)amino]-1H-indole-1-acetic acid

HRID 2233745Notes

Reaction equation

HRID 2233745 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:33]=[CH:32][C:7]([O:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:18][S:19]([CH3:22])(=[O:21])=[O:20])[N:11]([CH2:23][C:24]([O:26]C(C)(C)C)=[O:25])[C:10]=2[CH3:31])=[CH:6][CH:5]=1.O>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[NH:18][S:19]([CH3:22])(=[O:20])=[O:21])[N:11]([CH2:23][C:24]([OH:26])=[O:25])[C:10]=2[CH3:31])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium Hydroxide2×HCID 866092313-(4-Chlorophenoxy)-2-methyl-4-[(methylsulfonyl)amino]-1H-indole-1-acetic acid, 1,1-dimethylethyl ester

Product 1

HCID 116112153-(4-Chlorophenoxy)-2-methyl-4-[(methylsulfonyl)amino]-1H-indole-1-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 1M sodium hydroxide (0.5 ml) was added to a stirred mixture of the product from step (v) (40 mg) in THF (1 ml). After 3 h, further 1M sodium hydroxide (1 ml) was added and the reaction heated at 55° C. for 16 h. Water (10 ml) was added and the THF evaporated under reduced pressure. The solution was acidified with 2M hydrochloric acid and the resulting solid filtered off and dried. Yield 24 mg

Workup

  1. customthe THF evaporated under reduced pressure
  2. filtrationthe resulting solid filtered off
  3. customdried

Sources & evidence

ORD record
ord-933f1f84ed0f47e7becc83c9e33fb5b8
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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