Pyridine → HCID 131713917, compound

HRID 1632753Notes

Reaction equation

HRID 1632753 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].[CH2:43]([O:55][CH2:56][CH:57]([CH2:59][O:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])O)[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54].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[CH:31]([C:35]([O:37][CH:57]([CH2:56][O:55][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:59][O:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH3:72])=[O:36])[CH:32]=[CH:33][S:34][C@H:29]23)=[O:26])[N:23]=1)=[O:17]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 14630122HCID 14630122, compoundHCID 1317124427-[2-(2-Formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 131713917HCID 131713917, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dicyclohexylcarbodiimide (3.96 g) was added to a stirred solution of 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 6.58 g] and 2-n-dodecyloxy-1-n-dodecyloxymethylethanol (8.23 g) in a mixture of dry pyridine (60 ml) and dry tetrahydrofuran (20 ml) at 3° C., and then stirred at 0° to 5° C. for 4.75 hours and further at room temperature for an hour. The resultant mixture was poured into ice water (350 ml) and extracted with ethyl acetate (500 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 and 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 evaporating the solution in vacuo, the residue was subjected to column chromatography on silica gel (266 g) with a mixture of chloroform and methanol (20:1). The eluate was evaporated in vacuo to give powder [6.24 g] of 2-n-dodecyloxy-1-n-dodecyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-cephem-4-carboxylate (syn isomer).

Workup

  1. extractionextracted with ethyl acetate (500 ml)
  2. additionWater (50 ml) was added to the
  3. extractionextract
  4. customThe organic layer was separated
  5. washwashed with a saturated aqueous solution of sodium chloride (100 ml×2)
  6. dry with materialan aqueous solution of sodium bicarbonate in turn, and dried over anhydrous magnesium sulfate
  7. customAfter evaporating the solution in vacuo
  8. additionthe residue was subjected to column chromatography on silica gel (266 g) with a mixture of chloroform and methanol (20:1)
  9. customThe eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-668df398fb614cda9f39bbe596ba40d4
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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