Trifluoroacetic acid → (2S)-2-{3-[(4-methyl-1-benzothien-3-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}propanoic acid

HRID 1747389Notes

Reaction equation

HRID 1747389 reaction equation
C([O:5][C:6](=[O:30])[C@@H:7]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[C:20]3[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:21]=3[S:22][CH:23]=2)[C:10]1=[O:29])[CH3:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:28][C:27]1[C:20]2[C:19]([CH2:18][N:11]3[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[N:9]([C@@H:7]([CH3:8])[C:6]([OH:30])=[O:5])[C:10]3=[O:29])=[CH:23][S:22][C:21]=2[CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59497577(S)-2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid tert-butyl ester

Product 1

HCID 59497444(2S)-2-{3-[(4-methyl-1-benzothien-3-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}propanoic acidYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid tert-butyl ester (0.12 g, 0.28 mmol) in CH2Cl2 (5 mL) was added TFA (2 mL). The reaction mixture was stirred at room temperature for 3 h. When the reaction was complete, the reaction mixture was diluted with CH2Cl2 and washed with water. The organic phase was dried over Na2SO4 and concentrated. When a small amount of CH2Cl2 (˜3 mL) was added to the resulting residue, a white solid came out of the solution. This solid was filtered and dried to afford 69 mg (66%) of the titled compound. LCMS (ESMS): m/z 367.23 (M+H+).

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. additionWhen a small amount of CH2Cl2 (˜3 mL) was added to the resulting residue
  5. filtrationThis solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-c9c6fd3de05b44728c2e274914ac8856
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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