Sodium Azide → HCID 53771027, compound

HRID 978836Notes

Reaction equation

HRID 978836 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-a77e95312c6d4f50b38b1aa789c97e9b
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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