Trifluoroacetic acid → (S)-2-{[1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carbonyl]-amino}-4-methyl-pentanoic acid

HRID 1750166Notes

Reaction equation

HRID 1750166 reaction equation
C([O:5][C:6](=[O:35])[C@@H:7]([NH:12][C:13]([C:15]1[CH:34]=[CH:33][C:18]2[N:19]([CH:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[C:20]([CH2:22][CH:23]3[CH2:27][CH2:26][CH2:25][O:24]3)=[N:21][C:17]=2[CH:16]=1)=[O:14])[CH2:8][CH:9]([CH3:11])[CH3:10])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:29]([CH:28]([N:19]1[C:18]2[CH:33]=[CH:34][C:15]([C:13]([NH:12][C@@H:7]([CH2:8][CH:9]([CH3:10])[CH3:11])[C:6]([OH:35])=[O:5])=[O:14])=[CH:16][C:17]=2[N:21]=[C:20]1[CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][O:24]1)[CH2:31][CH3:32])[CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86714374(S)-2-{[1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carbonyl]-amino}-4-methyl-pentanoic acid tert-butyl ester

Product 1

HCID 86714376(S)-2-{[1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carbonyl]-amino}-4-methyl-pentanoic acidYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

75 mg of (S)-2-{[1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carbonyl]-amino}-4-methyl-pentanoic acid tert-butyl ester were dissolved in 0.6 ml dichloromethane and 0.18 μl of trifluoroacetic acid were added. After stirring at room temperature over night the reaction mixture was concentrated. The residue was dissolved in 1 M aqueous sodium hydroxide solution, and precipitated by addition of 2 M aqueous hydrochloric acid. The solid was taken up in ethyl acetate, dried over sodium sulphate and concentrated. The obtained residue was precipitated by addition of pentane. 23 mg (35%) of (S)-2-{[1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carbonyl]-amino}-4-methyl-pentanoic acid were obtained.

Workup

  1. concentrationwas concentrated
  2. dissolutionThe residue was dissolved in 1 M aqueous sodium hydroxide solution
  3. customprecipitated by addition of 2 M aqueous hydrochloric acid
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe obtained residue was precipitated by addition of pentane

Sources & evidence

ORD record
ord-db0290a734b24d95a0806e25176c30df
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

Loading…