Ethyl Acetate → HCID 129010382, compound

HRID 1904653Notes

Reaction equation

HRID 1904653 reaction equation
[Na+].[CH3:2][O:3][N:4]=[C:5]([C:29]1[N:30]=[C:31]([NH2:34])[S:32][CH:33]=1)[C:6]([NH:8][CH:9]1[C:27](=[O:28])[N:11]2[C:12]([C:24]([O-:26])=[O:25])=[C:13]([CH:16]=[CH:17][C:18]3[S:22][CH:21]=[N:20][C:19]=3[CH3:23])[CH2:14][S:15][C@H:10]12)=[O:7].[C:35]([O:41][CH2:42]I)(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37].C(OCC)(=O)C>CN(C)C=O>[C:35]([O:41][CH2:42][O:25][C:24]([C:12]1[N:11]2[C:27](=[O:28])[CH:9]([NH:8][C:6](=[O:7])[C:5](=[N:4][O:3][CH3:2])[C:29]3[N:30]=[C:31]([NH2:34])[S:32][CH:33]=3)[C@H:10]2[S:15][CH2:14][C:13]=1[CH:16]=[CH:17][C:18]1[S:22][CH:21]=[N:20][C:19]=1[CH3:23])=[O:26])(=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 104401Iodomethyl pivalateHCID 131715969HCID 131715969, compound

Product 1

HCID 129010382HCID 129010382, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

7-[2-Methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[2-(4-methylthiazol-5-yl)vinyl]-3-cephem-4-carboxylic acid sodium salt (syn-isomer, trans-isomer) (0.03 g, 0.06 mmol) was dissolved in dimethylformamide (3 ml). To the resultant solution was added a solution in dimethylformamide (1 ml) of iodomethyl pivalate (as prepared by reacting chloromethyl pivalate (0.090 g, 0.60 mmol) with sodium iodide (0.090 g, 0.06 mmol) in acetone) under ice-cooling, followed by stirring the resultant mixture for 10 minutes. The reaction solution as obtained were admixed with ice-water (20 ml) and ethyl acetate (20 ml), stirred thoroughly and then allowed to stand until the mixture separated into aqueous phase and organic phase. The organic phase was separated from the aqueous phase and washed twice with water (10 ml) and then with aqueous saturated NaCl solution (10 ml). The organic phase as washed was subsequently dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified chromatographically on a column of silica-gel (Wako-gel C-300) (5 g) as developed with ethyl acetate. The titled compound was thus obtained (yield 0.025 g, 67%).

Workup

  1. temperaturecooling
  2. customThe reaction solution as obtained
  3. customseparated into aqueous phase and organic phase
  4. customThe organic phase was separated from the aqueous phase
  5. washwashed twice with water (10 ml)
  6. washThe organic phase as washed
  7. dry with materialwas subsequently dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified chromatographically on a column of silica-gel (Wako-gel C-300) (5 g)

Sources & evidence

ORD record
ord-e1f894ef7f624ed688d3244db7fb8d71
Source dataset
uspto-grants-1989_06
Patent number
US04839350

Reaction notes

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