Triphenylphosphine → (S)-3-[6-Methyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-5-phenyl-pentanoic acid ethyl ester

HRID 1747295Notes

Reaction equation

HRID 1747295 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@@H:6]([N:15]1[C:19]2[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=2[NH:17][C:16]1=[O:25])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].[CH3:27][C:28]1[C:36]2[C:35]([CH2:37]O)=[CH:34][S:33][C:32]=2[CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C@@H:6]([N:15]1[C:19]2[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=2[N:17]([CH2:37][C:35]2[C:36]3[C:28]([CH3:27])=[CH:29][CH:30]=[CH:31][C:32]=3[S:33][CH:34]=2)[C:16]1=[O:25])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11148058(4-Methylbenzo[b]thiophen-3-yl)methanolHCID 59497622(S)-3-(6-Methyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-5-phenyl-pentanoic acid ethyl ester

Product 1

HCID 67543028(S)-3-[6-Methyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-5-phenyl-pentanoic acid ethyl esterYield 41.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-3-(6-Methyl-2-oxo-2,3-dihydro-benzimidazol-1-yl)-5-phenyl-pentanoic acid ethyl ester (0.2 g, 0.57 mmol), (4-Methyl-benzo[b]thiophen-3-yl)-methanol (0.10 g, 0.57 mmol), and triphenylphosphine (0.18 g, 0.68 mmol) was added dropwise DIAD (0.14 g, 0.68 mmol). The mixture was stirred at room temperature for 1 h. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over Na2SO4 and concentrated. The resulting oily residue was purified by prep TLC using 4:1 Hexane:EtOAc as an eluent to afford 0.12 g of the desired product as a brown oil.

Workup

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

Sources & evidence

ORD record
ord-66456a897fa547ee9430aa50fc3310f0
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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