Hydrochloric Acid → HCID 25027408, compound

HRID 238891Notes

Reaction equation

HRID 238891 reaction equation
C[O:2][C:3](=[O:31])[C:4]([CH3:30])([NH:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]2[CH:16]=[CH:15][S:14][C:13]=2[C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=1)=[O:8])[CH3:5].[Li+].[OH-].Cl>O1CCOCC1.C(OCC)(=O)C>[CH3:30][C:4]([NH:6][C:7]([C:9]1[CH:10]=[CH:11][C:12]2[CH:16]=[CH:15][S:14][C:13]=2[C:17]=1[O:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([F:28])([F:29])[F:27])=[CH:24][CH:25]=1)=[O:8])([CH3:5])[C:3]([OH:31])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68840442HCID 68840442, compound

Product 1

HCID 25027408HCID 25027408, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

308 mg 2-methyl-2-{[7-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-6-carbonyl]-amino}-propionic acid methyl ester was dissolved in 5 ml of 1,4-dioxane. To this was added 3.4 ml of 1 M LiOH (aq), and the reaction was stirred for 1 h at 60° C. and overnight at room temperature. The reaction mixture was diluted with 10 ml of ethyl acetate, acidified to pH 3 with 2N HCl (aq) and extracted with 10 ml ethyl acetate four times. The combined organic layers were washed with brine, dried over sodium sulphate and concentrated in vacuo to give 299 mg of 2-methyl-2-{[7-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-6-carbonyl]-amino}-propionic acid.

Workup

  1. extractionextracted with 10 ml ethyl acetate four times
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a238e5d0a0f74bb69083ccd4273b20eb
Source dataset
uspto-grants-2014_02
Patent number
US08642643B2

Reaction notes

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