Triphenylphosphine → HCID 59497701, compound

HRID 1747437Notes

Reaction equation

HRID 1747437 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15].[CH3:17][C:18]1[CH:19]=[C:20]2[N:25]([C:26]=1[CH3:27])[CH:24]=[CH:23][CH:22]=[C:21]2[CH2:28]O.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>C1COCC1.[Al]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH2:28][C:21]2[C:20]3[N:25]([C:26]([CH3:27])=[C:18]([CH3:17])[CH:19]=3)[CH:24]=[CH:23][CH:22]=2)[C:7]1=[O:15]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 59497358HCID 59497358, compoundHCID 59497624HCID 59497624, compound

Product 1

HCID 59497701HCID 59497701, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 5359268AluminumSolvent

Procedure

To a stirred solution of the 3-(2-oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester (100 mg, 0.45 mmol) and (2,3-Dimethyl-indolizin-8-yl)-methanol (88 mg, 0.50 mmol) in THF (8 ml) was added triphenylphosphine (143 mg, 0.54 mmol) followed by DIAD (0.11 ml, 0.54 mmol, dropwise) at ambient temperature. After five minutes the reaction became dark brown and was consequently wrapped in aluminum foil. After stirring over night the reaction was treated with silica gel and concentrated. The remaining solid was purified via column chromatography (silica gel, 5-40% EtOAc/hexanes). The product-containing fractions were combined and concentrated to give the product which was used without further purification.

Workup

  1. customat ambient temperature
  2. additionwas treated with silica gel
  3. concentrationconcentrated
  4. customThe remaining solid was purified via column chromatography (silica gel, 5-40% EtOAc/hexanes)
  5. concentrationconcentrated
  6. customto give the product which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-302f2cec82584d83870362dc59a19ea3
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…