Lithium Hydroxide → HCID 89518052, compound

HRID 571210Notes

Reaction equation

HRID 571210 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][C:23]([O:25]C)=[O:24])[CH:17]=[CH:16]2)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+]>O>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]([CH2:22][C:23]([OH:25])=[O:24])[CH:17]=[CH:16]2)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 89518049HCID 89518049, compound

Product 1

HCID 89518052HCID 89518052, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of methyl 2-(5-(N-(tert-butoxycarbonyl)methylsulfonamido)-1H-indol-1-yl)acetate (520 mg, 1.360 mmol) in a 1:1 mixture of THF and water (20 ml), lithium hydroxide (326 mg, 13.60 mmol) was added, and the mixture was reacted for 2 hours at room temperature. The organic layer was evaporated and 1N HCl was added to the reaction mixture (pH 5); the resulting solid was filtered off affording 2-(5-(N-(tert-butoxycarbonyl)methylsulfonamido)-1H-indol-1-yl)acetic acid that was used in the next step without any additional purification (450 mg, 1.221 mmol, 90% yield). MS/ESI+ 369.2 [MH]+.

Workup

  1. additionwas added
  2. customthe mixture was reacted for 2 hours at room temperature
  3. customThe organic layer was evaporated
  4. addition1N HCl was added to the reaction mixture (pH 5)
  5. filtrationthe resulting solid was filtered off

Sources & evidence

ORD record
ord-464566f2c61840c5b073973cc54668f7
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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