Potassium Iodide → HCID 70351204, compound

HRID 1708895Notes

Reaction equation

HRID 1708895 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:27](=[O:28])[N:11]2[C:12]([C:24]([OH:26])=[O:25])=[C:13]([CH2:16]OC(=O)CC(=O)C)[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:29]1[C:33]2[CH2:34][CH2:35][CH2:36][CH2:37][C:32]=2[N:31]=[CH:30]1.[I-].[K+].C(#N)C>C(OCC)(=O)C.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:27](=[O:28])[N:11]2[C:12]([C:24]([O-:26])=[O:25])=[C:13]([CH2:16][N+:31]3[C:32]4[CH2:37][CH2:36][CH2:35][CH2:34][C:33]=4[S:29][CH:30]=3)[CH2:14][S:15][C@H:10]12)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 13731266HCID 13731266, compoundHCID 67780351HCID 67780351, compound

Product 1

HCID 70351204HCID 70351204, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture consisting of 4.0 g of 7β-tert-butoxycarbonylamino-3-(3-oxobutyryloxymethyl]-3-cephem-4-carboxylic acid, 3.0 g of 4,5,6,7-tetrahydrobenzothiazole, 4 g of potassium iodide, 10 ml of acetonitrile and 10 ml of water is stirred at 70° C. for 1.5 hours. To the reaction mixture is added 30 ml of ethyl acetate and the mixture is stirred. After letting the mixture stand, the upper layer is removed by decanting. To the lower layer is added 30 ml of ethyl acetate and the same work-up is repeated twice. The water-layer is subjected to silica-gel column chromatography using 70 g of silica-gel. After washing of the column by using first 200 ml of acetone and then 200 ml of acetone-water (20:1), elution is conducted by acetone-water (3:1). The fractions containing the objective compound are concentrated and lyophilized to give 0.71 g (yield 15%) of the above-identified compound.

Workup

  1. stirringthe mixture is stirred
  2. customthe upper layer is removed
  3. customby decanting
  4. additionTo the lower layer is added 30 ml of ethyl acetate
  5. washAfter washing of the column
  6. wash200 ml of acetone-water (20:1), elution
  7. additionThe fractions containing the objective compound
  8. concentrationare concentrated

Sources & evidence

ORD record
ord-46d63a9f412842e1ad1cf3b8312a600d
Source dataset
uspto-grants-1990_08
Patent number
US04946837

Reaction notes

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