Piconol → HCID 70059335, compound

HRID 2230277Notes

Reaction equation

HRID 2230277 reaction equation
[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:16][C:17]([O:19][CH2:20][CH:21]1[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:27]2[C:22]1=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[CH2:41]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:34])[C@@H:7]([NH:16][C:17]([O:19][CH2:20][CH:21]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:27]=2[C:28]2[C:33]1=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:18])[CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:41][C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][N:35]=2)=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11474PiconolHCID 11776TriphenylphosphineHCID 15295906HCID 15295906, compound

Product 1

HCID 70059335HCID 70059335, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from Example G ((S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(4-hydroxyphenyl)-propionic acid tert-butyl ester) (4.00 g, 8.64 mmol), 2-pyridylcarbinol (0.92 mL, 9.50 mmol) and triphenylphosphine (2.24 g, 8.64 mmol) were dissolved in 50 mL of dry THF. The solution was cooled in an ice bath under an argon atmosphere and diethyl azidocarboxylate (1.36 mL, 8.64 mmol) was added dropwise over 20 minutes. The ice bath was removed and the solution allowed to stir overnight at room temperature. The solution was concentrated under reduced pressure and partitioned between ethyl acetate and water (100 mL each) and separated. The organic layer was washed with 10% aqueous HCl (2×50 mL), 10% sodium bicarbonate (2×50 mL), brine (2×50 mL), dried with magnesium sulfate, filtered, and concentrated under reduced pressure to a foam (4.80 g). The foam was purified by chromatography (silica gel, 1:1.5 ethyl acetate/hexane) to give the product as a white foam (3.90 g, 82%).

Workup

  1. temperatureThe solution was cooled in an ice bath under an argon atmosphere
  2. customThe ice bath was removed
  3. concentrationThe solution was concentrated under reduced pressure
  4. custompartitioned between ethyl acetate and water (100 mL each)
  5. customseparated
  6. washThe organic layer was washed with 10% aqueous HCl (2×50 mL), 10% sodium bicarbonate (2×50 mL), brine (2×50 mL)
  7. dry with materialdried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure to a foam (4.80 g)
  10. customThe foam was purified by chromatography (silica gel, 1:1.5 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8fd7942c0b6c4b89955e80289ef59d74
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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