Potassium Carbonate → (S)-2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid tert-butyl ester

HRID 1747391Notes

Reaction equation

HRID 1747391 reaction equation
[C:1]([O:5][C:6](=[O:21])[C@@H:7]([N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][C:12]1=[O:20])[CH2:8][CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[I-].C[N+](C)(C)[CH2:31][C:32]1[C:33]2[C:40]([CH3:41])=[CH:39][CH:38]=[CH:37][C:34]=2[S:35][CH:36]=1>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:21])[C@@H:7]([N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]([CH2:31][C:32]2[C:33]3[C:40]([CH3:41])=[CH:39][CH:38]=[CH:37][C:34]=3[S:35][CH:36]=2)[C:12]1=[O:20])[CH2:8][CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 59497589HCID 59497589, compoundHCID 85788499HCID 85788499, compound

Product 1

HCID 59497413(S)-2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanoic acid tert-butyl esterYield 71.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-2-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-pentanoic acid tert-butyl ester (0.1 g, 0.34 mmol) in DMF (2 mL) were added K2CO3 (0.1 g, 0.69 mmol) and trimethyl-(4-methyl-benzo[b]thiophen-3-ylmethyl)-ammonium iodide (0.24 g, 0.69 mmol). The reaction mixture was heated to 80° C. for 5 h. The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 0.11 g (71%) of the desired product as an oily residue. LCMS (ESMS): m/z 451.33 (M+H+).

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-6758d52424404a4b9b0e42be72c91d9f
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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