Lithium Hydroxide → HCID 121461939, compound

HRID 59741Notes

Reaction equation

HRID 59741 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([C:18]([O:20]CC)=[O:19])[S:16][CH:17]=1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6]([N:8]([C:13]1[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[S:16][CH:17]=1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 121461943HCID 121461943, compound

Product 1

HCID 121461939HCID 121461939, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of ethyl 4-(N-(tert-butoxycarbonyl)methylsulfonamido)-thiophene-2-carboxylate (Int. 43) (300 mg, 0.859 mmol) in THF/water 1/1 (20 ml), lithium hydroxide (61.7 mg, 2.58 mmol) was added, and the mixture was reacted overnight at RT. The organic solvent was evaporated and the aqueous residue was acidified with 1N HCl (pH=5); the resulting precipitate was collected by filtration yielding 4-(N-(tert-butoxycarbonyl)-methylsulfonamido)thiophene-2-carboxylic acid (Int. 44) (220 mg, 0.685 mmol, MS/ESI+343.7 [MNa]+).

Workup

  1. customthe mixture was reacted overnight at RT
  2. customThe organic solvent was evaporated
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-ac0398aaa7024ae4875d40d287e5bf6a
Source dataset
uspto-grants-2016_09
Patent number
US09440954B2

Reaction notes

Loading…