Triphenylphosphine → HCID 131722212, compound

HRID 1275167Notes

Reaction equation

HRID 1275167 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C@@H:11](O)[CH:12]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1)[N:13]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:15][OH:16])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9][CH2:10][C@H:11]1[O:16][CH2:15][CH2:14][N:13]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH:12]1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18712634HCID 18712634, compound

Product 1

HCID 131722212HCID 131722212, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

49.9 g (98.1 mmole) of 4-t-butyldimethylsilyloxy-(2 R)-(3,4-dichlorophenyl)-1-[N-(t-butoxycarbonyl)-N-(2-hydroxyethyl)amino]-2-butanol [prepared as described in step (a) above] and 30.9 g (118 mmole) of triphenylphosphine were dissolved in 600 ml of dried toluene. 51.3 g of a 40% w/v toluene solution containing 118 mmole of diethyl azodicarboxylate were added dropwise to the resulting solution at room temperature under a nitrogen atmosphere, and the mixture was stirred for 2 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 47:3 to 23:2 by volume as the eluent, to give 43.2 g of the title compound.

Workup

  1. additionwere added dropwise to the resulting solution at room temperature under a nitrogen atmosphere
  2. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography
  4. washa gradient elution method

Sources & evidence

ORD record
ord-d8cfce28f74243038d570ebbc3306a8e
Source dataset
uspto-grants-2000_12
Patent number
US06159967

Reaction notes

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