1H-1,2,4-Triazole → HCID 22277812, compound

HRID 1064033Notes

Reaction equation

HRID 1064033 reaction equation
[CH3:1][N:2]([CH2:10][CH2:11]O)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH:32]1[CH:36]=[N:35][CH:34]=[N:33]1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[CH3:1][N:2]([CH2:10][CH2:11][N:32]1[CH:36]=[N:35][CH:34]=[N:33]1)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

6

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 11776TriphenylphosphineHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 22277812HCID 22277812, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled solution (ice bath) of 2-[N-methyl-N-(t-butoxycarbonyl)amino]ethanol (J. Med. Chem., 1999, 42(11), 2007-2020; 5 g, 28 mmol), triphenyl phosphine (9.35 g, 36 mmol) and 1,2,4-triazole (1.64 g, 24 mmol) in DCM (30 ml) was added diethylazodicarboxylate (5.64 ml, 35.7 mmol) dropwise. The ice bath was removed and the reaction mixture allowed to stir at room temperature for 1 hour. The precipitate was discarded and the filtrate was concentrated and purified by flash chromatography, eluting with a 50% EtOAc/DCM and then 100% EtOAc to give a pale yellow oil which was used without further purification.

Workup

  1. customThe ice bath was removed
  2. concentrationthe filtrate was concentrated
  3. custompurified by flash chromatography
  4. washeluting with a 50% EtOAc/DCM
  5. custom100% EtOAc to give a pale yellow oil which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-f91701c5c5a8461eb48919d27514d702
Source dataset
uspto-grants-2005_11
Patent number
US06967216B2

Reaction notes

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