Triethylamine → HCID 12795449, compound

HRID 543596Notes

Reaction equation

HRID 543596 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10](=[O:31])[CH:11]([N:15]1[C@H:18]([S:19][S:20][C:21]2[S:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)[CH2:17][C:16]1=[O:30])[C:12](=[CH2:14])[CH3:13]>C(Cl)Cl>[CH3:8][O:9][C:10](=[O:31])[C:11]([N:15]1[C@H:18]([S:19][S:20][C:21]2[S:22][C:23]3[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)[CH2:17][C:16]1=[O:30])=[C:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 12795883HCID 12795883, compound

Product 1

HCID 12795449HCID 12795449, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 ml of triethylamine are added to a solution of 12 g of 2-[(4R)-4-(benzthiazol-2-yldithio)-2-oxoazetidin-1-yl]-3-methylenebutyric acid methyl ester in 500 ml of methylene chloride and the mixture is allowed to stand at room temperature for 90 minutes. The reaction mixture is washed with 5% aqueous citric acid solution, dried over sodium sulphate and freed of solvent in vacuo. The residue is purified by chromatography over silica gel (deactivated with 10% water) with toluene and toluene/ethyl acetate (19:1) and yields the title compound, which after recrystallisation from diethyl ether/pentane has a melting point of 63°-66°.

Workup

  1. washThe reaction mixture is washed with 5% aqueous citric acid solution
  2. dry with materialdried over sodium sulphate
  3. customThe residue is purified by chromatography over silica gel (deactivated with 10% water) with toluene and toluene/ethyl acetate (19:1)

Sources & evidence

ORD record
ord-6189a900b32d49f592f6912087a76d9b
Source dataset
uspto-grants-1984_05
Patent number
US04447360

Reaction notes

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