Hydrochloric Acid → (S)-3-Amino-N-(methylsulfonyl)-2-oxo-1-azetidinecarboxamide

HRID 279807Notes

Reaction equation

HRID 279807 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].CO.Cl>[Pd].O>[NH2:12][C@H:10]1[CH2:11][N:8]([C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[O:7])[C:9]1=[O:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 53997697(S)-N-(Methylsulfonyl)-2-oxo-3-[[(phenylmethoxy)-carbonyl]amino]-1-azetidinecarboxamide

Product 1

HCID 18602677(S)-3-Amino-N-(methylsulfonyl)-2-oxo-1-azetidinecarboxamideYield 45.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

(S)-N-(Methylsulfonyl)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinecarboxamide (2.20 g; see example 5) was stirred with 90 ml of methanol under nitrogen at 40° to 45° C. until solution occurs. The solutions was quickly cooled to room temperature and hydrogenated at one atmosphere in the presence of 1.1 g of 10% palladium on charcoal for twenty minutes. Water (20 ml) was added, and the pH was adjusted to 2.0 (1N hydrochloric acid). The product, which was absorbed on the catalyst, was collected by filtration, using Whatman #50 paper, and suspended in 25 ml of water. The pH was adjusted to 2.0 (1N hydrochloric acid), and the mixture was stirred for twenty-five minutes and filtered through Whatman #50 paper. Evaporation of the filtrate provided 611 mg of crystalline product, melting point 180° C., dec.

Workup

  1. customThe product, which was absorbed on the catalyst
  2. filtrationwas collected by filtration
  3. filtrationfiltered through Whatman #50 paper
  4. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-d15ab1ba14fb441fa587b552ad90dec7
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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