Methanol → HCID 54202767, compound

HRID 1275157Notes

Reaction equation

HRID 1275157 reaction equation
[N:1]([CH:4]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[C@H:5]([OH:16])[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)Cl.CO>O1CCCC1.O>[NH2:1][CH:4]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=1)[C@H:5]([OH:16])[CH2:6][CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 54373278HCID 54373278, compound

Product 1

HCID 54202767HCID 54202767, compoundYield 41.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

10.00 g (25.6 mmole) of 1-azido-4-t-butyldimethylsilyloxy-(2R)-(3,4-dichlorophenyl)-2-butanol [prepared as described in step (d) above] were dissolved in 100 ml of tetrahydrofuran and 0.6 ml of water, and 7.39 g (28.2 mmole) of triphenylphosphine were added to the resulting solution. The mixture was then stirred under a nitrogen atmosphere at 80° C. for 4 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, hexane was added to the resulting residue and the deposited crystals were removed by filtration. The filtrate was concentrated by evaporation under reduced pressure, and the resulting residue was purified by silica gel flash column chromatography, using a gradient elution method, with mixtures of methylene chloride and methanol ranging from 30:1 to 10:1 by volume as the eluent, to obtain 3.83 g (yield 41%) of the title compound as a colorless oil.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure, hexane
  2. additionwas added to the resulting residue
  3. customthe deposited crystals were removed by filtration
  4. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  5. customthe resulting residue was purified by silica gel flash column chromatography
  6. washa gradient elution method

Sources & evidence

ORD record
ord-dae1696a8849437fb6e0733fdd007332
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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