Trifluoroacetic acid → 2-Methyl-2-{[4-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acid

HRID 238894Notes

Reaction equation

HRID 238894 reaction equation
C([O:5][C:6](=[O:34])[C:7]([CH3:33])([NH:9][C:10]([C:12]1[CH:20]=[CH:19][C:15]2[S:16][CH:17]=[CH:18][C:14]=2[C:13]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)=[O:11])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:33][C:7]([NH:9][C:10]([C:12]1[CH:20]=[CH:19][C:15]2[S:16][CH:17]=[CH:18][C:14]=2[C:13]=1[O:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]([F:31])([F:32])[F:30])=[CH:27][CH:28]=1)=[O:11])([CH3:8])[C:6]([OH:34])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 688447032-Methyl-2-{[4-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acid tert-butyl ester

Product 1

HCID 250274072-Methyl-2-{[4-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acidYield 64.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

113 mg of 2-Methyl-2-{[4-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acid tert-butyl ester were dissolved in 2 ml dichloromethane and treated with 2 ml trifluoroacetic acid. After 30 min at 60° C. the volatiles were evaporated. The residue was treated with ethanol and 2 M HCl and evaporated three times. The resulting residue was crystallized from diethylether/heptane to afford 65 mg of 2-Methyl-2-{[4-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acid.

Workup

  1. customAfter 30 min at 60° C. the volatiles were evaporated
  2. additionThe residue was treated with ethanol and 2 M HCl
  3. customevaporated three times
  4. customThe resulting residue was crystallized from diethylether/heptane

Sources & evidence

ORD record
ord-26583c8e3a99486f8c4049acc8e786d4
Source dataset
uspto-grants-2014_02
Patent number
US08642643B2

Reaction notes

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