Ammonia → HCID 54262037, compound

HRID 1585817Notes

Reaction equation

HRID 1585817 reaction equation
C([O:4][C@@H:5]1[C@H:8]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[NH:7][C:6]1=[O:14])(=O)C.N>CO>[OH:4][C@@H:5]1[C@H:8]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[NH:7][C:6]1=[O:14]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15224366HCID 15224366, compound

Product 1

HCID 54262037HCID 54262037, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of 3.88 g of (3R,4R)-3-acetoxy-4-(2-thienyl)-2-azetidinone in 60 cm3 of methanol is injected a stream of anhydrous ammonia gas at a temperature in the region of 5° C. for one hour with stirring. The reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The residual solid is purified by chromatography on 180 g of silica (0.063-0.2 mm) contained in a column of diameter 4 cm [eluent: dichloromethane/methanol (95/5 by volume)], collecting 10 cm3 fractions. The fractions containing only the desired product are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. 2.24 g of (3R,4R)-3-hydroxy-4-(2-thienyl)-2-azetidinone are obtained in the form of white crystals melting at 174° C. and for which the physical characteristics are the following:

Workup

  1. customin the region of 5° C.
  2. customfor one hour
  3. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) at 40° C
  4. customThe residual solid is purified by chromatography on 180 g of silica (0.063-0.2 mm)
  5. customcollecting 10 cm3 fractions
  6. additionThe fractions containing only the desired product
  7. concentrationconcentrated to dryness under reduced pressure (2.7 kPa) at 40° C

Sources & evidence

ORD record
ord-574bdcbe39c44a149f6cd0e018a17b48
Source dataset
uspto-grants-1999_08
Patent number
US05939561

Reaction notes

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