Triphenylphosphine → 2,2-Dimethyl-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester

HRID 1747326Notes

Reaction equation

HRID 1747326 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]3=[O:21])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C:24](=[O:30])[C:25]([CH3:29])([CH3:28])[CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:22][O:23][C:24](=[O:30])[C:25]([CH3:29])([CH3:28])[CH2:26][N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:9]2[C:10]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=3[S:7][CH:8]=2)[C:13]1=[O:21]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 84152Methyl 3-hydroxypivalateHCID 594973791-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 594976752,2-Dimethyl-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl esterYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (50 mg, 0.17 mmol), 3-Hydroxy-2,2-dimethyl-propionic acid methyl ester (0.026 mL, 0.20 mmol) and triphenylphosphine (53 mg, 0.20 mmol) in dry THF (1.5 mL) is added diisopropyl azodicarboxylate (0.041 mL, 0.20 mmol) in a drop wise manner. The mixture is stirred at room temperature for 40 hrs. Then the solvent is removed under vacuum and the residue is purified by two preparative TLC's (first one is developed with 30% EtOAc in Hexanes, second one is developed with 1% MeOH in CH2Cl2) to give 28 mg (41%) of 2,2-Dimethyl-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester.

Workup

  1. customThen the solvent is removed under vacuum
  2. customthe residue is purified by two preparative TLC's (first one is developed with 30% EtOAc in Hexanes, second one is developed with 1% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-f8f81140dfec4f01a7d4b29f0c2ed3ab
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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