Hydrochloric Acid → (S)-N-(Methylsulfonyl)-2-oxo-3-amino-1-azetidinecarboxamide, hydrochloride salt

HRID 279805Notes

Reaction equation

HRID 279805 reaction equation
[CH3:1][S:2]([NH:5][C:6]([N:8]1[CH2:11][C@H:10]([NH:12]C(OCC2C=CC=CC=2)=O)[C:9]1=[O:23])=[O:7])(=[O:4])=[O:3].[ClH:24]>CO.[Pd].O>[ClH:24].[CH3:1][S:2]([NH:5][C:6]([N:8]1[CH2:11][C@H:10]([NH2:12])[C:9]1=[O:23])=[O:7])(=[O:3])=[O:4]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 53997697(S)-N-(Methylsulfonyl)-2-oxo-3-[[(phenylmethoxy)-carbonyl]amino]-1-azetidinecarboxamide

Product 1

HCID 131714659(S)-N-(Methylsulfonyl)-2-oxo-3-amino-1-azetidinecarboxamide, hydrochloride salt

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 300 mg of (S)-N-(methylsulfonyl)-2-oxo-3-[[(phenylmethoxy)carbonyl]-amino-1-azetidinecarboxamide (see example 5) in 8 ml of dry methanol was added 150 mg of 10% palladium on charcoal. The mixture was hydrogenated at room temperature and 1 atmosphere for 30 minutes, and then 2 ml of water was added followed by dilute hydrochloric acid to adjust the pH to 1.8. The catalyst was filtered using water/methanol. Evaporation of the filtrate gave 65 mg of crude product. The catalyst was suspended in water, adjusted to pH 1.8 and stirred at room temperature for 15 minutes. Removal of the catalyst and evaporation of the filtrate provided additional crude product (124 mg).

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered
  3. customEvaporation of the filtrate
  4. customgave 65 mg of crude product
  5. customRemoval of the catalyst and evaporation of the filtrate

Sources & evidence

ORD record
ord-7d1a898abff24f45b1815eab72db747d
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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