HCID 53896214, compound → HCID 53766169, compound

HRID 621074Notes

Reaction equation

HRID 621074 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].CSC(=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 86740397HCID 86740397, 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 monomethyldithiocarbamate 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-b8f38b350d3e461698774faa8ea3460e
Source dataset
uspto-grants-1989_04
Patent number
US04822788

Reaction notes

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