Hydrochloric Acid → (2S,3R)-3-azido-4-oxo-2-azetidinecarboxylic acid

HRID 2413710Notes

Reaction equation

HRID 2413710 reaction equation
[Si]([N:8]1[C:11](=[O:12])[C@H:10]([N:13]=[N+:14]=[N-:15])[C@H:9]1[C:16]([OH:18])=[O:17])(C(C)(C)C)(C)C.Cl.[OH-].[Na+]>CO.CN(C=O)C>[N:13]([C@H:10]1[C:11](=[O:12])[NH:8][C@@H:9]1[C:16]([OH:18])=[O:17])=[N+:14]=[N-:15]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13712291(2S,3R)-1-t-butyldimethylsilyl-3-azido-4-oxo-2-azetidinecarboxylic acid

Product 1

HCID 13712293(2S,3R)-3-azido-4-oxo-2-azetidinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

In 39 ml of methanol was dissolved 1.78 g of compound (23) and 9.85 ml of 1N hydrochloric acid was added to the solution. The mixture was stirred for 1.75 hours at room temperature. The reaction mixture was cooled to 0° C. and 9.85 ml of 1N sodium hydroxide was added thereto. The mixture was concentrated to dryness under reduced pressure to obtain an oil. The oil was dissolved in 10 ml of DMF and 3A molecular sieve was added thereto. After the mixture was allowed to stand overnight, the solvent was removed by distillation under reduced pressure to obtain (2S,3R)-3-azido-4-oxo-2-azetidinecarboxylic acid (24). This compound was used in the following Example 7 as it was.

Workup

  1. additionwas added to the solution
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. concentrationThe mixture was concentrated to dryness under reduced pressure
  4. customto obtain an oil
  5. waitto stand overnight
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-eef52db0d70043b1a034e928c151ab6a
Source dataset
uspto-grants-1988_01
Patent number
US04719207

Reaction notes

Loading…