Pyridine → HCID 131713913, compound

HRID 1632749Notes

Reaction equation

HRID 1632749 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH:16]([NH:18][C:19]1[S:20][CH:21]=[C:22]([C:24](=[N:40][O:41][CH3:42])[C:25]([NH:27][CH:28]2[C:38](=[O:39])[N:30]3[C:31]([C:35]([OH:37])=[O:36])=[CH:32][CH2:33][S:34][C@H:29]23)=[O:26])[N:23]=1)=[O:17].[C:43]([O:53][CH2:54][CH:55]([CH2:57][O:58][C:59](=[O:68])[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])O)(=[O:52])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51].N1C=CC=CC=1>O1CCCC1>[CH:16]([NH:18][C:19]1[S:20][CH:21]=[C:22]([C:24](=[N:40][O:41][CH3:42])[C:25]([NH:27][CH:28]2[C:38](=[O:39])[N:30]3[C:31]([C:35]([O:37][CH:55]([CH2:54][O:53][C:43](=[O:52])[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])[CH2:57][O:58][C:59](=[O:68])[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH3:67])=[O:36])=[CH:32][CH2:33][S:34][C@H:29]23)=[O:26])[N:23]=1)=[O:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 13038804HCID 13038804, compoundHCID 1317124427-[2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 131713913HCID 131713913, compoundYield 28.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dicyclohexylcarbodiimide (6.5 g) was added to a stirred solution of 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 8.6 g) and 2-n-nonanoyloxy-1-n-nonanoyloxymethylethanol (7.8 g) in a mixture of dry pyridine (80 ml) and dry tetrahydrofuran (25 ml) at 3° C., and then stirred at 0° to 5° C. for 4 hours and allowed to stand at room temperature overnight. The resultant mixture was poured into ice water (450 ml) and extracted with ethyl acetate (450 ml). Water (50 ml) was added to the extract and adjusted to pH 2 to 3 with 20% sulfuric acid. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride (100 ml×2) and an aqueous solution of sodium bicarbonate in turn, and dried over anhydrous magnesium sulfate. After removing the solution in vacuo, the residue was subjected to column chromatography on silica gel (370 g) with a mixture of chloroform and acetone (5:1). The eluate was evaporated in vacuo to give powder (4.62 g) of 2-n-nonanoyloxy-1-n-nonanoyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer).

Workup

  1. waitto stand at room temperature overnight
  2. extractionextracted with ethyl acetate (450 ml)
  3. additionWater (50 ml) was added to the
  4. extractionextract
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride (100 ml×2)
  7. dry with materialan aqueous solution of sodium bicarbonate in turn, and dried over anhydrous magnesium sulfate
  8. customAfter removing the solution in vacuo
  9. additionthe residue was subjected to column chromatography on silica gel (370 g) with a mixture of chloroform and acetone (5:1)
  10. customThe eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-817e6319f30a49a7987e3d714a3c69c9
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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