Lithium hydroxide, monohydrate → 5-[2-(3-Hydroxy-phenyl)-ethyl-carbamoyl]-3-methyl-thiophene-2-carboxylic acid

HRID 1952570Notes

Reaction equation

HRID 1952570 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:11](=[O:22])[NH:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[CH:8][C:9]=1[CH3:10])=[O:4].O[Li].O>C1COCC1.O>[OH:21][C:17]1[CH:16]=[C:15]([CH2:14][CH2:13][NH:12][C:11]([C:7]2[S:6][C:5]([C:3]([OH:4])=[O:2])=[C:9]([CH3:10])[CH:8]=2)=[O:22])[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 682267035-[2-(3-Hydroxy-phenyl)-ethyl-carbamoyl]-3-methyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 682270555-[2-(3-Hydroxy-phenyl)-ethyl-carbamoyl]-3-methyl-thiophene-2-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

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

Procedure

A solution of 5-[2-(3-hydroxy-phenyl)-ethyl-carbamoyl]-3-methyl-thiophene-2-carboxylic acid methyl ester (260 mg, 0.81 mmol) in THF/water (8 ml/4 ml) was treated with LiOH.H2O (171 mg, 4.1 mmol) at 40° C. for 1.5 h. The reaction mixture was quenched with 1N HCl and extracted with EtOAc. The layers were separated. The organic layer was washed with brine, then dried over Na2SO4 and concentrated under reduced pressure to afford the desired product (172 mg, 70% 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 washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5d19167f7bec4886b1f4aebee937fd21
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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