Water → HCID 131712606, compound

HRID 1659790Notes

Reaction equation

HRID 1659790 reaction equation
[C:1]([O:8][CH2:9]I)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH3:11][O:12][N:13]=[C:14]([C:37]1[N:38]=[C:39]([NH2:42])[S:40][CH:41]=1)[C:15]([NH:17][CH:18]1[C:35](=[O:36])[N:20]2[C:21]([C:32]([O-:34])=[O:33])=[C:22]([CH2:25][S:26][C:27]3[S:28][CH:29]=[N:30][N:31]=3)[CH2:23][S:24][C@H:19]12)=[O:16].[Na+].O.C(OCC)(=O)C>CN(C)C=O>[CH3:11][O:12][N:13]=[C:14]([C:37]1[N:38]=[C:39]([NH2:42])[S:40][CH:41]=1)[C:15]([NH:17][CH:18]1[C:35](=[O:36])[N:20]2[C:21]([C:32]([O:34][CH2:9][O:8][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[O:33])=[C:22]([CH2:25][S:26][C:27]3[S:28][CH:29]=[N:30][N:31]=3)[CH2:23][S:24][C@H:19]12)=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12775069Iodomethyl hexanoateHCID 131712607HCID 131712607, compound

Product 1

HCID 131712606HCID 131712606, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of iodomethyl hexanoate (1.58 g.) in dimethylformamide (3 ml.) was added at a time under ice-cooling to a stirred solution of sodium 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (3.0 g.) in dimethylformamide (15 ml.). The mixture was stirred for 10 minutes at the same temperature and poured into a mixture of water (50 ml.) and ethyl acetate (100 ml.). The aqueous layer was separated and extracted twice with ethyl acetate (50 ml.). The combined ethyl acetate layer was filtered and the filtrate was washed three times with an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo to a volume of 20 ml. to give precipitates, which were collected by filtration, washed with ethyl acetate (10 ml.) and dried to give hexanoyloxymethyl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (2.1 g.).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted twice with ethyl acetate (50 ml.)
  3. filtrationThe combined ethyl acetate layer was filtered
  4. washthe filtrate was washed three times with an aqueous solution of sodium bicarbonate
  5. dry with materiala saturated aqueous solution of sodium chloride and dried over magnesium sulfate
  6. concentrationThe solution was concentrated in vacuo to a volume of 20 ml
  7. customto give
  8. customprecipitates
  9. filtrationwhich were collected by filtration
  10. washwashed with ethyl acetate (10 ml.)
  11. customdried

Sources & evidence

ORD record
ord-f351c89790374096babb2773d64aa244
Source dataset
uspto-grants-1981_12
Patent number
US04304770

Reaction notes

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