Lithium Hydroxide → 4-[1-({[5-Chloro-3-(3-chlorobenzyl)-2-thienyl]carbonyl}amino)ethyl]-benzoic acid

HRID 870036Notes

Reaction equation

HRID 870036 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH:10]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)[CH3:11])=[O:8])=[C:4]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH:3]=1.[Li+].[OH-]>C1COCC1.CO>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH:10]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([OH:18])=[O:17])=[CH:20][CH:21]=2)[CH3:11])=[O:8])=[C:4]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 45140205Methyl 4-[1-({[5-chloro-3-(3-chlorobenzyl)-2-thienyl]carbonyl}amino)ethyl]benzoate

Product 1

HCID 249525754-[1-({[5-Chloro-3-(3-chlorobenzyl)-2-thienyl]carbonyl}amino)ethyl]-benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 4-[1-({[5-chloro-3-(3-chlorobenzyl)-2-thienyl]carbonyl}amino)ethyl]benzoate from Example 1, Step 10 (81.0 mg, 0.181 mmol) and LiOH (0.9 mL, 1M in water) in THF (1.5 mL) and methanol (1.5 mL) was stirred overnight at r.t. and concentrated. The residue was diluted with 1N HCl and extracted with EtOAc. The organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give the desired product as a white solid. MS (−ESI): m/z 432.0 (M−1)−.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with 1N HCl
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-820e357dc3c4446da24808c47394bb62
Source dataset
uspto-grants-2015_03
Patent number
US08969394B2

Reaction notes

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