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

HRID 874748Notes

Reaction equation

HRID 874748 reaction equation
C([O:5][C:6](=[O:32])[C:7]([CH3:31])([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]COC1C=CC=CC=1)=[O:11])[CH3:8])(C)(C)C.[F:33][C:34]([F:39])([F:38])[C:35](O)=O>ClCCl>[CH3:8][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:12]1[CH:20]=[CH:19][C:35]([C:34]([F:39])([F:38])[F:33])=[CH:14][CH:13]=1)=[O:11])([CH3:31])[C:6]([OH:5])=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 688422062-Methyl-2-{[4-(2-phenoxy-ethoxy)-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 acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

113 mg of 2-Methyl-2-{[4-(2-phenoxy-ethoxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acid tert-butyl ester were dissolved in 2 ml dichloromethane and treated with 1 ml trifluoroacetic acid. After 6h at room temperature 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 50 mg of 2-Methyl-2-{[4-(4-trifluoromethyl-benzyloxy)-benzo[b]thiophene-5-carbonyl]-amino}-propionic acid.

Workup

  1. customAfter 6h at room temperature 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-f43cc7495e9f463eb919b8eb9c25855e
Source dataset
uspto-grants-2015_03
Patent number
US08980938B2

Reaction notes

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