Lithium hydroxide, monohydrate → 5-[(1H-indol-4-ylmethyl)-carbamoyl]-3-methyl-thiophene-2-carboxylic acid

HRID 1952567Notes

Reaction equation

HRID 1952567 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:11](=[O:23])[NH:12][CH2:13][C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[CH:17][NH:18]3)=[CH:8][C:9]=1[CH3:10])=[O:4].O[Li].O>C1COCC1.O>[NH:18]1[C:19]2[C:15](=[C:14]([CH2:13][NH:12][C:11]([C:7]3[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([CH3:10])[CH:8]=3)=[O:23])[CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:17]1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 682268105-[(1H-indol-4-ylmethyl)-carbamoyl]-3-methyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682264395-[(1H-indol-4-ylmethyl)-carbamoyl]-3-methyl-thiophene-2-carboxylic acidYield 114.5%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 5-[(1H-indol-4-ylmethyl)-carbamoyl]-3-methyl-thiophene-2-carboxylic acid methyl ester (115 mg, 0.35 mmol) in THF/water (6 ml/3 ml) was treated with LiOH.H2O (157 mg, 3.5 mmol) at rt for 24 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 (126 mg, 100% 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-fec0ca4fa5c747b2a34a9e24ba95d88e
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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