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

HRID 1747388Notes

Reaction equation

HRID 1747388 reaction equation
[C:1]([O:5][C:6](=[O:19])[C@@H:7]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]1=[O:18])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[CH3:20][C:21]1[C:29]2[C:28]([CH2:30]O)=[CH:27][S:26][C:25]=2[CH:24]=[CH:23][CH:22]=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>[C:1]([O:5][C:6](=[O:19])[C@@H:7]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:30][C:28]2[C:29]3[C:21]([CH3:20])=[CH:22][CH:23]=[CH:24][C:25]=3[S:26][CH:27]=2)[C:10]1=[O:18])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11148058(4-Methylbenzo[b]thiophen-3-yl)methanolHCID 59497411(S)-2-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid tert-butyl ester

Product 1

HCID 59497577(S)-2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid tert-butyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid tert-butyl ester (0.3 g, 0.46 mmol), (4-Methyl-benzo[b]thiophen-3-yl)-methanol (0.12 g, 0.69 mmol), and triphenylphosphine (0.14 g, 0.55 mmol) was added dropwise DIAD (0.11 mL, 0.55 mmoL) at 0° C. The mixture was slowly warmed to room temperature and stirred for 2 h. The reaction mixture was diluted with ethyl acetate and washed with water (×2). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 4:1 Hexanes:ethyl acetate as an eluent to afford 0.12 g (62%) of the desired product as a brownish oil. This product was not pure (˜70% pure by 1H-NMR), but was used for the next reaction without further purification.

Workup

  1. washwashed with water (×2)
  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-757ab58e91af4efa944fc82a4b3d346a
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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