Acetone → HCID 70606383, compound

HRID 1415411Notes

Reaction equation

HRID 1415411 reaction equation
[C:1]1(=[O:24])[N:5]([CH:6]2[C:17](=[O:18])[N:8]3[C:9]([C:14]([OH:16])=[O:15])=[C:10]([CH3:13])[CH2:11][S:12][C@H:7]23)[C:4](=[O:19])[C:3]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:2]12.[CH3:25]C(C)=O>O>[C:4]1(=[O:19])[N:5]([CH:6]2[C:17](=[O:18])[N:8]3[C:9]([C:14]([O:16][CH3:25])=[O:15])=[C:10]([CH3:13])[CH2:11][S:12][C@H:7]23)[C:1](=[O:24])[C:2]2=[CH:23][CH:22]=[CH:21][CH:20]=[C:3]12

Participants

4

Reactant 2

HCID 180AcetoneHCID 70474055HCID 70474055, compound

Product 1

HCID 70606383HCID 70606383, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 17.3 g. (0.05 mol.) of 7-phthalimido-3-methyl-3-cephem-4-carboxylic acid in 50 ml. of acetone and 20 ml. of water, 5 g. (0.05 mol.) of KHCO3 were slowly added. The resulting solution was evaporated to dryness, and 38 ml. of DMF and 5 ml. of methyl iodide were added to the residue. The mixture was stirred for 3 hrs. at room temperature. To this mixture were then added 100 g. of ice, and the resulting solid product was filtered. The product was crystallized from a mixture of 100 ml. of 2-propanol and 100 ml. of acetone. Yield: 7.91 of crystals, m.p. 187°-188°; ir (CHCl3) 1790 and 1735 cm-1, nmr (CDCl3) δ 2.31 (s, 3, CH3), 3.0 and 3.75 (ABq, 2, J=15 Hz), 3.85 (s, 3, CH3), 5.15 (d, 1, J=4.4 Hz), 5.74 (d, 1, J=4.4 Hz) and 7.73 (m, 4, ArH).

Workup

  1. customThe resulting solution was evaporated to dryness, and 38 ml
  2. additionof methyl iodide were added to the residue
  3. customat room temperature
  4. additionTo this mixture were then added 100 g
  5. filtrationof ice, and the resulting solid product was filtered
  6. customThe product was crystallized from a mixture of 100 ml

Sources & evidence

ORD record
ord-e6ec38556e814337b1f52df8a9ce88b6
Source dataset
uspto-grants-1977_01
Patent number
US04005074

Reaction notes

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