Triphenylphosphine → HCID 59104364, compound

HRID 2307796Notes

Reaction equation

HRID 2307796 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[C:9]([O:13][C:14](=[O:25])[NH:15][CH:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17]O)([CH3:12])([CH3:11])[CH3:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[C:9]([O:13][C:14](=[O:25])[NH:15][C@@H:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:17][O:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH3:10])([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5995293-Bromo-5-hydroxypyridineHCID 5050210HCID 5050210, compound

Product 1

HCID 59104364HCID 59104364, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-bromo-pyridin-3-ol (0.3 g, 1.7 mmol), (2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester (0.41 g 1.7 mmol), and triphenylphosphine (0.52 g, 2 mmol) in THF (15 mL) was stirred at 0° C. for 30 min. To the mixture was added a solution of di-t-butyl azidodicarboxylate (0.46 g, 2 mmol) in 5 ml of THF. The mixture was allowed to warm to room temperature then stirred at room temperature for 20 h. The THF was evaporated off and the residue was taken into ethyl acetate (75 ml), washed with saturated sodium bicarbonate (50 ml) water (50 ml) and brine (50 ml). The ethyl acetate was evaporated off and the residue was purified by flash column chromatography on silica gel, eluting with a solvent gradient of 1:4 to 1:2 ethyl acetate/hexane. Recovered 0.82 g of a mixture of product and di-tert-butyl azidodicarboxylate. MS (ESI) m/z 395 (M+H)+.

Workup

  1. customThe THF was evaporated off
  2. washwashed with saturated sodium bicarbonate (50 ml) water (50 ml) and brine (50 ml)
  3. customThe ethyl acetate was evaporated off
  4. customthe residue was purified by flash column chromatography on silica gel
  5. washeluting with a solvent gradient of 1:4 to 1:2 ethyl acetate/hexane
  6. customRecovered 0.82 g of a mixture of product and di-tert-butyl azidodicarboxylate

Sources & evidence

ORD record
ord-167cf5625c5347b5bc16ca0c2200a23e
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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