Diisopropyl Ether → HCID 131713914, compound

HRID 1632750Notes

Reaction equation

HRID 1632750 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([OH:20])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1.C(N(CC)CC)C.[CH:33]1([C:39]([O:41][CH2:42]I)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C(OC(C)C)(C)C>CS(C)=O.CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:23][O:24][CH3:25])[C:8]([NH:10][CH:11]2[C:21](=[O:22])[N:13]3[C:14]([C:18]([O:20][CH2:42][O:41][C:39]([CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[O:40])=[O:19])=[CH:15][CH2:16][S:17][C@H:12]23)=[O:9])[N:6]=1

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 11010989HCID 11010989, compoundHCID 1317124447-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 131713914HCID 131713914, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 6.0 g) was dissolved in a mixed solution of dry dimethylsulfoxide (90 ml) and dry dimethylformamide (30 ml). After adding triethylamine (1.58 g) to the stirred solution at 9° C. over 2 minutes, iodomethyl cyclohexanecarboxylate (4.2 g) was added thereto with stirring over 5 minutes, and then stirred under ice cooling for 35 minutes. Ice water (500 ml) was added to the resultant solution and extracted with ethyl acetate three times. The solution was subsequently washed with a diluted aqueous solution of sodium bicarbonate, an aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solution was evaporated in vacuo, and the residue was purified by column chromatography on silica gel (100 g) with a mixed solution of chloroform and acetone (10:3). The eluate was evaporated in vacuo to give the purified residue. The residue was pulverized with diisopropyl ether and dried in vacuo to give cyclohexylcarbonyloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 4.0 g).

Workup

  1. stirringstirred under ice cooling for 35 minutes
  2. extractionextracted with ethyl acetate three times
  3. washThe solution was subsequently washed with a diluted aqueous solution of sodium bicarbonate
  4. dry with materialan aqueous solution of sodium thiosulfate and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  5. customThe solution was evaporated in vacuo
  6. customthe residue was purified by column chromatography on silica gel (100 g) with a mixed solution of chloroform and acetone (10:3)
  7. customThe eluate was evaporated in vacuo
  8. customto give the purified residue
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b72df08351834a56bb9c32beee6729b1
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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