Dimethyl Sulfoxide → HCID 67780351, compound

HRID 1708893Notes

Reaction equation

HRID 1708893 reaction equation
CS(C)=O.[NH2:5][C@@H:6]1[C:24](=[O:25])[N:8]2[C:9]([C:21]([OH:23])=[O:22])=[C:10]([CH2:13][O:14][C:15](=[O:20])[CH2:16][C:17](=[O:19])[CH3:18])[CH2:11][S:12][C@H:7]12.[C:26](=O)([O:32]C(C)(C)C)[O:27][C:28]([CH3:31])([CH3:30])[CH3:29].O>C(OCC)(=O)C>[C:28]([O:27][C:26]([NH:5][C@@H:6]1[C:24](=[O:25])[N:8]2[C:9]([C:21]([OH:23])=[O:22])=[C:10]([CH2:13][O:14][C:15](=[O:20])[CH2:16][C:17](=[O:19])[CH3:18])[CH2:11][S:12][C@H:7]12)=[O:32])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 117819897beta-Amino-3(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid

Product 1

HCID 67780351HCID 67780351, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 500 ml of dimethyl sulfoxide is added 200 g of 7β-amino-3-(3-oxobutyryloxymethyl)-3-cephem-4-carboxylic acid. To this 200 g of di-tert-butyl carbonate is added at room temperature and the mixture is stirred for 16 hours. To the reaction mixture are added 200 g of ice, 2 liters of water and 1 liter of ethyl acetate, and the mixture is stirred. After phase separation, the upper layer is discarded. To the aqueous layer is added 1 liter of ethyl acetate, and 129 g of phosphoric acid is added dropwise thereto while stirring (pH 4). After thorough mixing, the upper layer is separated and the lower layer is extracted with 1 liter of ethyl acetate. The organic layers are combined, washed with two 2-liter portions of ice-water and then with 1 liter of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated. To the residue is added 100 ml of methylene chloride, and the resulting mixture is concentrated and dried to give 194 g (74% yield) of the above-identified compound as a glassy solid.

Workup

  1. stirringthe mixture is stirred
  2. customAfter phase separation
  3. additionTo the aqueous layer is added 1 liter of ethyl acetate, and 129 g of phosphoric acid
  4. additionis added dropwise
  5. stirringwhile stirring (pH 4)
  6. customAfter thorough mixing, the upper layer is separated
  7. extractionthe lower layer is extracted with 1 liter of ethyl acetate
  8. washwashed with two 2-liter portions of ice-water
  9. dry with materialwith 1 liter of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. additionTo the residue is added 100 ml of methylene chloride
  12. concentrationthe resulting mixture is concentrated
  13. customdried

Sources & evidence

ORD record
ord-9942ad7f22e5464b94ddfc452a523e63
Source dataset
uspto-grants-1990_08
Patent number
US04946837

Reaction notes

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