Sodium Chloride → HCID 57124250, compound

HRID 620983Notes

Reaction equation

HRID 620983 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-methoxyiminoacetamido]-2-oxoazetidine(syn-isomer, cis-trans mixture). IR νmaxKBr cm-1 ; 3275, 2100, 1765, 1665, 1540.

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-f517c45b4f7e45a38788be0ffe7dc767
Source dataset
uspto-grants-1989_04
Patent number
US04822790

Reaction notes

Loading…