Triphenylphosphine → HCID 57517512, compound

HRID 2368148Notes

Reaction equation

HRID 2368148 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].O[CH2:13][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:15][C@@H:14]([NH:16][C:17]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:23])[CH3:13])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 960094-HydroxyphenylacetateHCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Product 1

HCID 57517512HCID 57517512, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-hydroxyphenyl acetate (60.8 g), tert-butyl [(1S)-2-hydroxy-1-methylethyl]carbamate (70 g) and triphenylphosphine (105 g) in THF (300 mL) was added dropwise a solution (1.9 M, 210 mL) of diisopropyl azodicarboxylate in toluene at 0° C., and the mixture was stirred at room temperature for 16 hr. The reaction mixture was concentrated under reduced pressure, the residue was suspended in diethyl ether, and the precipitate was removed by filtration. The filtrate was concentrated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate), and then by silica gel chromatography (NH, hexane/ethyl acetate) to give the title compound (70.9 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe precipitate was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2b2b656ae3d7451f9559d2062bf8bbf7
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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