Lithium hydroxide, monohydrate → HCID 68226849, compound

HRID 1952568Notes

Reaction equation

HRID 1952568 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:11](=[O:24])[NH:12][CH2:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][C:17](=[O:23])[NH:18]3)=[CH:8][C:9]=1[CH3:10])=[O:4].O[Li].O>C1COCC1.O>[CH3:10][C:9]1[CH:8]=[C:7]([C:11](=[O:24])[NH:12][CH2:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH2:16][C:17](=[O:23])[NH:18]3)[S:6][C:5]=1[C:3]([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68226790HCID 68226790, compound

Product 1

HCID 68226849HCID 68226849, compoundYield 95%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 3-methyl-5-[(2-oxo-2,3-dihydro-1H-indol-4-ylmethyl)-carbamoyl]-thiophene-2-carboxylic acid methyl ester (158 mg, 0.46 mmol) in THF/water (6 ml/3 ml) was treated with LiOH.H2O (206 mg, 4.6 mmol) at rt for 1 h. The reaction mixture was quenched with 1N HCl and extracted with EtOAc. The layers were separated. The organic layer was successively washed with water and brine, then dried over Na2SO4 and concentrated under reduced pressure to afford the desired product (141 mg, 95% yield).

Workup

  1. customThe reaction mixture was quenched with 1N HCl
  2. extractionextracted with EtOAc
  3. customThe layers were separated
  4. washThe organic layer was successively washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0ca1b4e818e845149f0ec854d66d62fb
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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