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

HRID 2055337Notes

Reaction equation

HRID 2055337 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-f2b0c3d9c9f74157986c93b3387f4cd2
Source dataset
uspto-grants-2008_02
Patent number
US07332492B2

Reaction notes

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