Carbon tetrabromide → tert-Butyl [(5-methyl-1,3,4-oxadiazol-2-yl)methyl]carbamate

HRID 2071061Notes

Reaction equation

HRID 2071061 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(=C1N=CC=N1)=O.[C:20]([NH:23][NH2:24])(=O)[CH3:21].C(Br)(Br)(Br)Br.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[CH3:21][C:20]1[O:12][C:10]([CH2:9][NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[N:24][N:23]=1

Participants

7

Reactant 5

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 14039AcetohydrazideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 13571086Carbonylimidazole

Product 1

HCID 57366760tert-Butyl [(5-methyl-1,3,4-oxadiazol-2-yl)methyl]carbamateYield 107.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of Boc-Glycine (1.75 g, 10.0 mmol) in CH2Cl2 at 0° C. was added carbonyl imidazole (1.7 g, 10.5 mmol) and the reaction was stirred for 30 min and then acetic hydrazide (740 mg, 10.0 mmol) was added. After 45 min, CBr4 (6.63 g, 20.0 mmol) and PPh3 (5.25 g, 20.0 mmol) were added and the reaction was stirred overnight at room temperature. The reaction mixture was concentrated partially and chromatographed (50% EtOAc in hexanes) to provide 2.3 g of tert-butyl (5-methyl-1,3,4-oxadiazol-2-yl)methylcarbamate with some triphenylphosphine oxide as impurity.

Workup

  1. waitAfter 45 min
  2. stirringthe reaction was stirred overnight at room temperature
  3. concentrationThe reaction mixture was concentrated partially
  4. customchromatographed (50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d0362ba986db4ab38717d9d120190627
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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