HCID 53896214, compound → HCID 53766169, compound

HRID 653242Notes

Reaction equation

HRID 653242 reaction equation
[C:1]([O:4][C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11](=[O:26])[C:12]([C:16]1[N:17]=[C:18]([NH:21]C(=O)CCl)[S:19][CH:20]=1)=[N:13][O:14][CH3:15])(=[O:3])[CH3:2].COC(=S)N.[Na]>CN(C=O)C>[C:1]([O:4][C@@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:11](=[O:26])[C:12]([C:16]1[N:17]=[C:18]([NH2:21])[S:19][CH:20]=1)=[N:13][O:14][CH3:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 53896214HCID 53896214, compoundHCID 86741498HCID 86741498, compound

Product 1

HCID 53766169HCID 53766169, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 500 mg of (3S,4S)-4-acetoxy-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-oxoazetidine (syn-isomer) in 10 ml of DMF is added 0.245 g of sodium monomethyithiocarbamate and the mixture is stirred at room temperature for one hour. The solvent is distilled off under reduced pressure, the residue is washed three times with ethyl acetate and the insolubles are filtered off after addition of ethanol. The filtrate is concentrated under reduced pressure. Then, purifying the residue on a silica gel column (ethyl acetate:CHCl3 :CH3OH=2:2:1) yields 0.270 g of (3S,4S)-4-acetoxy-3-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-2-oxoazetidine (syn-isomer).

Workup

  1. distillationThe solvent is distilled off under reduced pressure
  2. washthe residue is washed three times with ethyl acetate
  3. filtrationthe insolubles are filtered off
  4. additionafter addition of ethanol
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customThen, purifying the residue on a silica gel column (ethyl acetate:CHCl3 :CH3OH=2:2:1)

Sources & evidence

ORD record
ord-b4512651226e49388ef54c7dd4b0beaa
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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