HCID 12834136, compound → HCID 131711253, compound

HRID 1660602Notes

Reaction equation

HRID 1660602 reaction equation
[CH2:1]([CH2:4][C:5](Cl)=[S:6])[CH:2]=[CH2:3].[CH3:8][CH:9]1[CH:14]=[C:13]([C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:21])[Cl:20])=[O:16])[N:12]2[C:23](=[O:26])[CH:24]([NH2:25])[C@H:11]2[S:10]1>ClCCl>[CH3:8][CH:9]1[CH:14]=[C:13]([C:15]([O:17][CH2:18][C:19]([Cl:22])([Cl:20])[Cl:21])=[O:16])[N:12]2[C:23](=[O:26])[CH:24]([NH:25][C:5](=[S:6])[CH2:4][CH2:1][CH:2]=[CH2:3])[C@H:11]2[S:10]1

Participants

4

Reactant 2

HCID 12834136HCID 12834136, compoundHCID 19755419HCID 19755419, compound

Product 1

HCID 131711253HCID 131711253, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a suspension of 2,2,2-trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate hydrochloride (0.764 g) in dried dichloromethane (8 ml) were added at -30° C. a solution of triethylamine (0.18 g) in dichloromethane (2 ml) and then a solution of dimethylaniline (0.27 g) in dichloromethane (2 ml). While, allylthioacetate acid (0.528 g) was added to thionyl chloride (5 ml) and the mixture was allowed to stand for 20 minutes at room temperature and 5 minutes at 50° C., after which thionyl chloride was removed under reduced pressure, and the residue was added a small amount of benzene, and then removed under reduced pressure to give allylthioacetyl chloride (0.527 g). A solution of this obtained allylthioacetyl chloride (0.452 g) in dichloromethane (3 ml) was dropwise added at -30° C. over 5 minutes to the above-mentioned solution of 2,2,2-trichloroethyl 2-methyl-7-amino-3-cephem-4-carboxylate, and the mixture was stirred for 1 hour at -20° C. After the reaction, the reaction mixture was in turn washed twice with 5% hydrochloric acid, once with water, twice with a saturated sodium bicarbonate aqueous solution and once with a saturated sodium chloride aqueous solution, and dried over magnesium sulfate. After the solvent was distilled off, the residue (0.82 g) was recrystallized from a mixture of ether and isopropyl ether to give 2,2,2-trichloroethyl 2-methyl-7-(2-allylthioacetamido)-3-cephem-4-carboxylate (0.71 g), mp 96° C.

Workup

  1. customAfter the reaction
  2. washwashed twice with 5% hydrochloric acid, once with water, twice with a saturated sodium bicarbonate aqueous solution and once with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. distillationAfter the solvent was distilled off
  5. customthe residue (0.82 g) was recrystallized from a mixture of ether and isopropyl ether

Sources & evidence

ORD record
ord-da001a4d48264d04841224a9c8a94d17
Source dataset
uspto-grants-1981_12
Patent number
US04308380

Reaction notes

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