Pyridine → 2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-3-methylcrotonic acid 2,2,2-trichloroethyl ester

HRID 2309085Notes

Reaction equation

HRID 2309085 reaction equation
[Cl:1][C:2]([Cl:30])([Cl:29])[CH2:3][O:4][C:5](=[O:28])[C:6]([N:10]1[C@H:13]([S:14]SC2SC3C=CC=CC=3N=2)[C@@H:12]([O:25][CH3:26])[C:11]1=[O:27])=[C:7]([CH3:9])[CH3:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1.[C:56](OC(=O)C)(=[O:58])[CH3:57]>C(O)(=O)C>[Cl:30][C:2]([Cl:1])([Cl:29])[CH2:3][O:4][C:5](=[O:28])[C:6]([N:10]1[C@H:13]([S:14][C:56](=[O:58])[CH3:57])[C@@H:12]([O:25][CH3:26])[C:11]1=[O:27])=[C:7]([CH3:8])[CH3:9]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11776TriphenylphosphineHCID 867417822-[(3S,4R)-4-(benzthiazol-2-yldithio)-3-methoxy-2-oxoazetidin-1-yl]-3-methylcrotonic acid 2,2,2-trichloroethyl ester

Product 1

HCID 867417812-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-3-methylcrotonic acid 2,2,2-trichloroethyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.26 g of 2-[(3S,4R)-4-(benzthiazol-2-yldithio)-3-methoxy-2-oxoazetidin-1-yl]-3-methylcrotonic acid 2,2,2-trichloroethyl ester in 36.3 ml of acetic anhydride and 12.4 ml of acetic acid is cooled to -15° and 1.7 g of triphenylphosphine are added. After stirring under nitrogen at the same temperature for 75 minutes, 24.8 ml of pyridine are added to the mixture. After stirring for a further 3 hours at 0°, the reaction mixture is concentrated by evaporation under reduced pressure and the resulting residue is purified by chromatography over silica gel with toluene and toluene/ethyl acetate (19:1). IR spectrum (in methylene chloride): characteristic absorption bands at 3.40, 5.63, 5.77, 5.80, 6.13, 7.25, 7.35, 8.26, 9.0, 9.52 and 11.90μ.

Workup

  1. stirringAfter stirring for a further 3 hours at 0°
  2. concentrationthe reaction mixture is concentrated by evaporation under reduced pressure
  3. customthe resulting residue is purified by chromatography over silica gel with toluene and toluene/ethyl acetate (19:1)
  4. customIR spectrum (in methylene chloride): characteristic absorption bands at 3.40, 5.63, 5.77, 5.80, 6.13, 7.25, 7.35, 8.26, 9.0, 9.52 and 11.90μ

Sources & evidence

ORD record
ord-e7dcff836ebc4963b670a28f8f1f98d1
Source dataset
uspto-grants-1987_09
Patent number
US04692442

Reaction notes

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