1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86650594, compound

HRID 1257400Notes

Reaction equation

HRID 1257400 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[C:9]([CH2:17]O)[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=2)=[N:4][C:3]=1[CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.N12CCCN=C1CCCCC2.C1(P([N:52]=[N+:53]=[N-:54])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[N:52]([CH2:17][C:9]1[CH:8]=[C:7]([C:5]2[S:6][C:2]([CH3:1])=[C:3]([CH2:19][O:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][O:22]3)[N:4]=2)[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=1)=[N+:53]=[N-:54]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 66939196HCID 66939196, compound

Product 1

HCID 86650594HCID 86650594, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (7 mL) of the compound (1.3 g, 3.4 mmol) obtained in Example 95c in tetrahydrofuran were added 1,8-diazabicyclo[5.4.0]undec-7-ene (0.61 mL, 4.1 mmol) and diphenylphosphoryl azide (1.1 g, 4.1 mmol), and the mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=85/15) to give the title compound (1.1 g, 80%) as a colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=85/15)

Sources & evidence

ORD record
ord-676e55f578354c1ab6462c6ade752042
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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