Phenylacetyl chloride → (S)-N-(Methylsulfonyl)-2-oxo-3-[(phenylacetyl)-amino]-1-azetidinecarboxamide

HRID 279806Notes

Reaction equation

HRID 279806 reaction equation
Cl.[CH3:2][S:3]([NH:6][C:7]([N:9]1[CH2:12][C@H:11]([NH2:13])[C:10]1=[O:14])=[O:8])(=[O:5])=[O:4].[C:15]1([CH2:21][C:22](Cl)=[O:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[OH-].[K+]>C(#N)C.C(N(CC)CC)C>[CH3:2][S:3]([NH:6][C:7]([N:9]1[CH2:12][C@H:11]([NH:13][C:22](=[O:23])[CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10]1=[O:14])=[O:8])(=[O:4])=[O:5]

Participants

7

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 14797Potassium HydroxideHCID 62657Potassium Phosphate, TribasicHCID 131714659(S)-N-(Methylsulfonyl)-2-oxo-3-amino-1-azetidinecarboxamide, hydrochloride salt

Product 1

HCID 13631272(S)-N-(Methylsulfonyl)-2-oxo-3-[(phenylacetyl)-amino]-1-azetidinecarboxamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
5 °C

Procedure

(S)-N-Methylsulfonyl)-2-oxo-3-amino-1-azetidinecarboxamide, hydrochloride salt (189 mg; see example 6) was suspended in 8 ml of dry acetonitrile and 0.54 ml of triethylamine, and stirred at room temperature under nitrogen until solution occurred (about 15 minutes). The solution was cooled to 0°to 5° C., and then phenyl acetylchloride (153 μl) was added. The reaction was stirred at room temperature for 3 hours and then poured into 10 ml of 0.5 M pH 5.5 monobasic potassium phosphate buffer. The pH was adjusted to 7 (dilute potassium hydroxide) and the solution was extracted twice with ethyl acetate. The aqueous layer was covered with fresh ethyl acetate, and the pH was adjusted to 2 (3N hydrochloric acid). Repeated extraction with ethyl acetate gave an acidic ethyl acetate extract, which was dried (sodium sulfate) and evaporated to a residue (196 mg). Chromatography of this material on 20 g of SilicAR CC-4 using ethyl acetate/dichloromethane (1:1) provides 96 mg of crystalline product after removal of solvent. Recrystallization from ethyl acetate/dichloromethane provides an analytical sample having a melting point 168°-170° C., dec.

Workup

  1. custom(about 15 minutes)
  2. extractionthe solution was extracted twice with ethyl acetate
  3. extractionextraction with ethyl acetate
  4. customgave an acidic ethyl acetate
  5. extractionextract
  6. dry with materialwhich was dried (sodium sulfate)
  7. customevaporated to a residue (196 mg)

Sources & evidence

ORD record
ord-1e4eecf4491743efbb58cf0c19200870
Source dataset
uspto-grants-1986_05
Patent number
US04587047

Reaction notes

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