Water → HCID 117987842, compound

HRID 2206074Notes

Reaction equation

HRID 2206074 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)[N:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][C@@H:8]2[CH3:12])[CH:6]=1.C(N(CC)CC)C.C1(P([N:39]=[N+:40]=[N-:41])(C2C=CC=CC=2)=O)C=CC=CC=1.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4](/[CH:13]=[CH:14]/[C:15]([N:39]=[N+:40]=[N-:41])=[O:17])[N:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][C@@H:8]2[CH3:12])[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 117988034HCID 117988034, compound

Product 1

HCID 117987842HCID 117987842, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (2E)-3-(4-bromo-1-(cis-2-methylcyclopentyl)-1H-pyrrol-2-yl)acrylic acid (700 mg) in DMF (7 mL) was added a solution of triethylamine (0.36 mL) and diphenylphosphoryl azide (0.678 g) in DMF (1 mL) at room temperature, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (685 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a34c7451d8ea4326b89859c1fc636500
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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