Triphenylphosphine → HCID 66999479, compound

HRID 559326Notes

Reaction equation

HRID 559326 reaction equation
[C:1]([O:5][C:6](=[O:20])[N:7]([CH2:12][C:13](=[O:19])[NH:14][CH2:15][CH2:16][CH:17]=[CH2:18])[C@H:8]([CH3:11])[CH2:9]O)([CH3:4])([CH3:3])[CH3:2].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>O1CCCC1>[C:1]([O:5][C:6]([N:7]1[CH2:12][C:13](=[O:19])[N:14]([CH2:15][CH2:16][CH:17]=[CH2:18])[CH2:9][C@H:8]1[CH3:11])=[O:20])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86626320HCID 86626320, compound

Product 1

HCID 66999479HCID 66999479, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A solution of but-3-enylcarbamoylmethyl-((R)-2-hydroxy-1-methyl ethyl)-carbamic acid tert-butyl ester (4.26 g, 14.9 mmol) in tetrahydrofuran (200 ml) was added dropwise at <10° C. to a mixture of triphenylphosphine (5.07 g, 19.3 mmol) and diisopropyl azodicarboxylate (3.91 g, 19.3 mmol), then the reaction mixture was heated at 60° C. for 2 h. After cooling and evaporation of volatile material, the residue was chromatographed (SiO2; heptane-ethyl acetate gradient) to afford the title compound (2.51 g, 63%). Yellow oil, MS (ISP)=269.3 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. customevaporation of volatile material
  3. customthe residue was chromatographed (SiO2; heptane-ethyl acetate gradient)

Sources & evidence

ORD record
ord-d58d78c67f594c638bda16d7fde1b957
Source dataset
uspto-grants-2011_11
Patent number
US08063042B2

Reaction notes

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