1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18672376, compound

HRID 1058271Notes

Reaction equation

HRID 1058271 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:12]=1[CH2:13]O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCN2C(=NCCC2)CC1.C1C=CC(P([N:45]=[N+:46]=[N-:47])(C2C=CC=CC=2)=O)=CC=1>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:11]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:12]=1[CH2:13][N:45]=[N+:46]=[N-:47])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 69939028HCID 69939028, compound

Product 1

HCID 18672376HCID 18672376, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of 2-(1-(tert-butyloxycarbonylamino)ethyl)-5-chlorobenzyl alcohol from the previous step (0.475 g, 1.67 mmol) in toluene (20.0 mL) at ambient temperature under nitrogen atmosphere was added DBU (0.26 mL g, 1.74 mmol) and DPPA (0.43 mL, 2.0 mmol). The mixture was stirred at ambient temperature for 72 h. The reaction was concentrated in vacuo then partitioned between EtOAc and water. The EtOAc layer was separated, dried over anhydrous Na2SO4, and filtered. The filtrate solvent was removed under reduced pressure and the residue purified by flash silica gel chromatography using dichloromethane as an eluent. 2-(1-(tert-butyloxycarbonylamino)ethyl)-5-chlorobenzylazide was obtained as a yellow oil after concentration of desired fractions in vacuo (0.53 g; HPLC RT=3.71 min, method A).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthen partitioned between EtOAc and water
  3. customThe EtOAc layer was separated
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customThe filtrate solvent was removed under reduced pressure
  7. customthe residue purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-0bea57b76c0f4c87a74a04350868ff9d
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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