Sodium Azide → HCID 53771027, compound

HRID 465192Notes

Reaction equation

HRID 465192 reaction equation
C(O[C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=O)C.[N-:30]=[N+:31]=[N-:32].[Na+]>CO.O>[N:30]([C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[N+:31]=[N-:32]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 53918863HCID 53918863, compound

Product 1

HCID 53771027HCID 53771027, compoundYield 35.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3.0 g of (3S,4S)-4-acetoxy-3-tritylamino-2-oxoazetidine in 50 ml of methanol is added a solution of 0.65 g of sodium azide in 5 ml of water under ice-cooling, followed by stirring for two hours at 40°-50° C. The solvent is distilled off under reduced pressure. To the residue is added ethyl acetate, and the organic layer is separated, which is washed with water and concentrated. The residue is purified on a silica-gel column (ethyl acetate: n-hexane=1:1) to give 1.01 g of (3S,4R)-4-azido-3-tritylamino-2-oxoazetidine.

Workup

  1. temperaturecooling
  2. distillationThe solvent is distilled off under reduced pressure
  3. additionTo the residue is added ethyl acetate
  4. customthe organic layer is separated
  5. washwhich is washed with water
  6. concentrationconcentrated
  7. customThe residue is purified on a silica-gel column (ethyl acetate: n-hexane=1:1)

Sources & evidence

ORD record
ord-02182ebd8f83460b89d2511ba4728a09
Source dataset
uspto-grants-1985_10
Patent number
US04550105

Reaction notes

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