Oxalyl chloride → HCID 19361920, compound

HRID 376458Notes

Reaction equation

HRID 376458 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([Cl:18])=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 27559811-Boc-Azetidine-3-carboxylic acid

Product 1

HCID 19361920HCID 19361920, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

1-tert-Butyloxycarbonyl-azetidine-3-carboxylic acid (345 mg) in dry dichloromethane (10 ml) was treated with oxalyl chloride (254 mg; 0.175 ml) and N,N-dimethylformamide (1 drop). The solution was stirred for 1.5 hours, and then the solvent was removed by evaporation under reduced pressure. The residue was dissolved in toluene (10 ml), and the toluene was evaporation under reduced pressure to give 1-tert-butyloxycarbonyl-azetidine-3-carbonyl chloride as a colourless oil. The oil was dissolved in dichloromethane (6 ml) and the solution was treated with silver cyanate (525 mg). The mixture was stirred for 10 minutes, and then mutilin 11-trifluoroacetate (535 mg) in dichloromethane (9 ml) was added. The mixture was stirred for 20 hours. Ethyl acetate (50 ml) was added and the mixture was filtered. The filtrate was washed with saturated sodium bicarbonate solution (20 ml) and saturated sodium chloride solution (20 ml). The solution was dried (sodium sulphate) and the solvent was removed under reduced pressure to yield a colourless gum. The gum was chromatographed on silica gel using 1:4 to 1:2 ethyl acetate/hexane to give the title compound as a colourless gum (485 mg); 1H NMR (CDCl3) inter alia 1.43 (9H, s), 3.93 (1H, quin, J 7.2 Hz), 4.98 (1H, d, J 6.9 Hz), 4.14 (4H, m), 5.23 (1H, d, J 17.5 Hz), 5.29 (1H, d, J 11.2 Hz), 5.58 (1H, d, J 8 Hz), 6.31 (1H, dd, J 17.5, 11.2 Hz), 7.57 (1H, s).

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. dissolutionThe residue was dissolved in toluene (10 ml)
  3. customevaporation under reduced pressure

Sources & evidence

ORD record
ord-4a35372bda2146fd88417d6698455409
Source dataset
uspto-grants-2000_02
Patent number
US06020368

Reaction notes

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