Triphenylphosphine → HCID 66654534, compound

HRID 517697Notes

Reaction equation

HRID 517697 reaction equation
[C:1]([O:4][CH2:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)=O)(=[O: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.C[Si]([N:54]=[N+:55]=[N-:56])(C)C>O1CCCC1>[C:1]([O:4][CH2:5][C:6]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=2)[N:56]=[N:55][N:54]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 78378AzidotrimethylsilaneHCID 2107996HCID 2107996, compound2×

Product 1

HCID 66654534HCID 66654534, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[(4-cyanophenyl)amino]-2-oxoethyl acetate (3.48 g, 15.95 mmol, Intermediate 7) in tetrahydrofuran (THF) (200 mL) was added triphenylphosphine (8.37 g, 31.9 mmol), di-isopropyl azodicarboxylate (6.20 mL, 31.9 mmol) and trimethylsilylazide (4.23 mL, 31.9 mmol). The reaction mixture was stirred at room temperature for 18 hours. The majority of the solvent was removed under vacuum and the residue purified by silica chromatography (Biotage SP4, eluting 30% EtOAc in iso-hexane (5 column volumes) then a gradient from 30-40% ethyl acetate in iso-hexane (over 7 column volumes)) to yield the title compound as a white solid (2.68 g).

Workup

  1. customThe majority of the solvent was removed under vacuum
  2. customthe residue purified by silica chromatography (Biotage SP4
  3. washeluting 30% EtOAc in iso-hexane (5 column volumes)

Sources & evidence

ORD record
ord-5aa8bc47dc1d4f9bb429028e5e8acbfa
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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