Sodium Iodide → 2-n-Octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 1632755Notes

Reaction equation

HRID 1632755 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH:14]([NH:16][C:17]1[S:18][CH:19]=[C:20]([C:22](=[N:60][O:61][CH3:62])[C:23]([NH:25][CH:26]2[C:58](=[O:59])[N:28]3[C:29]([C:34]([O:36][CH:37]([CH2:48][O:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[O:35])=[CH:30][CH2:31][S:32](=O)[C@H:27]23)=[O:24])[N:21]=1)=[O:15].[I-].[Na+]>CC(C)=O>[CH:14]([NH:16][C:17]1[S:18][CH:19]=[C:20]([C:22](=[N:60][O:61][CH3:62])[C:23]([NH:25][CH:26]2[C:58](=[O:59])[N:28]3[C:29]([C:34]([O:36][CH:37]([CH2:38][O:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:48][O:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])=[O:35])=[CH:30][CH2:31][S:32][C@H:27]23)=[O:24])[N:21]=1)=[O:15]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 9845Trifluoroacetic anhydrideHCID 1317139182-n-Octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 1317139192-n-Octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylateYield 68.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,2,2-Trifluoroacetic anhydride (2.12 g) was dropwise added to a stirred solution of 2-n-octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate-1-oxide (syn isomer, 2.34 g) and sodium iodide (1.56 g) in dry acetone (40 ml) at 0° to 5° C. over 45 minutes, and stirred at 0° to 5° C. for 2 hours. The resultant mixture was poured into ice water (200 ml), and then extracted with ethyl acetate (110 ml). The extract was washed with an aqueous solution of sodium thiosulfate, an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, and then dried over anhydrous magnesium sulfate. After evaporating the solution in vacuo, the residue was subjected to column chromatography, on silica gel (100 g) with a mixture of chloroform and methanol (20:1). The eluate was evaporated in vacuo to give powder (1.57 g) of 2-n-octyloxy-1-n-octyloxymethylethyl 7-[2-(2-formamidothiazol-4 -yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 1.57 g).

Workup

  1. extractionextracted with ethyl acetate (110 ml)
  2. washThe extract was washed with an aqueous solution of sodium thiosulfate
  3. dry with materialan aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in turn, and then dried over anhydrous magnesium sulfate
  4. customAfter evaporating the solution in vacuo
  5. additionthe residue was subjected to column chromatography, on silica gel (100 g) with a mixture of chloroform and methanol (20:1)
  6. customThe eluate was evaporated in vacuo

Sources & evidence

ORD record
ord-3b0755829d0144f59408dc682c16813b
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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