Sodium Chloride → HCID 57124250, compound

HRID 2231520Notes

Reaction equation

HRID 2231520 reaction equation
C([O:4][C@@H:5]1[NH:8][C:7](=O)[C@H:6]1[NH:10][C:11](=[O:26])[C:12]([C:16]1[N:17]=[C:18]([NH:21][C:22](=[O:25])[CH2:23][Cl:24])[S:19][CH:20]=1)=[N:13][O:14][CH3:15])(=O)C.[N-:27]=[N+:28]=[N-:29].[Na+].C(OCC)(=O)C.[Cl-].[Na+]>CN(C=O)C.O>[N:27]([CH:7]1[NH:8][C:5](=[O:4])[C@H:6]1[NH:10][C:11](=[O:26])[C:12]([C:16]1[N:17]=[C:18]([NH:21][C:22](=[O:25])[CH2:23][Cl:24])[S:19][CH:20]=1)=[N:13][O:14][CH3:15])=[N+:28]=[N-:29]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 53896214HCID 53896214, compound

Product 1

HCID 57124250HCID 57124250, compoundYield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.380 g of (3S,4S)-4-acetoxy-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-oxoazetidine in 1 ml of DMF is added a solution of 0.079 g of sodium azide in 1 ml of water and the mixture is stirred at room temperature for 15 hours. After addition of ethyl acetate and saturated aqueous sodium chloride solution, the organic layer is separated and washed with aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. Purifying the residue on a silica gel column (ethyl acetate:CHCl3 :CH3OH=4:4:1) yields 0.201 g of (3S)-4-azido-3-[2-(2-chloroacetamidothiazol-4-yl)-2-methoxyimino-acetamido]-2-oxoazetidine(syn-isomer, cis-trans mixture).

Workup

  1. customthe organic layer is separated
  2. washwashed with aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurifying the residue on a silica gel column (ethyl acetate:CHCl3 :CH3OH=4:4:1)

Sources & evidence

ORD record
ord-403283bc8b714f7b846ac723c3798b8f
Source dataset
uspto-grants-1988_11
Patent number
US04782147

Reaction notes

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