Sodium Azide → HCID 14808129, compound

HRID 654057Notes

Reaction equation

HRID 654057 reaction equation
Cl[CH2:2][CH2:3][CH:4]([OH:16])[CH:5]([N:11]1[CH2:14][CH2:13][C:12]1=[O:15])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[N-:17]=[N+:18]=[N-:19].[Na+]>CS(C)=O.ClCCl>[N:17]([CH2:2][CH2:3][CH:4]([OH:16])[CH:5]([N:11]1[CH2:14][CH2:13][C:12]1=[O:15])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 14808128HCID 14808128, compound

Product 1

HCID 14808129HCID 14808129, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 5-chloro-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate (3.45 g, 13.8 mmol) and sodium azide (1.10 g, 17 mmol) in dry dimethylsulphoxide (20 ml) was stirred between 55° and 65° C. for 5 hours. The reaction mixture was diluted with dichloromethane and the organic layer was washed three times with water before being dried (MgSO4) and evaporated. The residue was chromatographed on silica gel (Merck Art. 9385), eluting with ethyl acetate/hexane (2:1), to give ethyl 5-azido-3-hydroxy-2-(2-oxoazetidin-1-yl)valerate as a pale yellow oil in 73% yield (2.59 g). Bulb to bulb distillation at 0.2 mmHg between 185°-195° C. further purified the product to a colourless oil. νmax (KBr) 3405, 2102 and 1733 cm-1 ; δH (CHCl3, 250 MHz) 1.31 (3H,t,J 7 Hz), 1.81 (1H,m), 1.87 (1H,m), 3.03 (2H,t,J 3 Hz), 3.40 (2H,m), 3.53 (2H,m), 4.00 (1H,d,J 3.5 Hz), 4.25 (3H,m) and 4.53 (1H,d,J 4.5 Hz, exchangeable). (Found: C, 46.93; H, 6.46; N, 21.83%. C10H16N3O4 requires C,46.87; H, 6.29; N, 21.86%).

Workup

  1. washthe organic layer was washed three times with water
  2. dry with materialbefore being dried (MgSO4)
  3. customevaporated
  4. customThe residue was chromatographed on silica gel (Merck Art. 9385)
  5. washeluting with ethyl acetate/hexane (2:1)

Sources & evidence

ORD record
ord-de9612ba4cd2489db30e09c27d4c33d4
Source dataset
uspto-grants-1992_07
Patent number
US05130241

Reaction notes

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