Acetic Acid → HCID 131713136, compound

HRID 647460Notes

Reaction equation

HRID 647460 reaction equation
CO.O1CCCC1.C(O)(=O)C.[C:12]([O:16][C:17]([CH2:19][O:20][N:21]=[C:22]([C:49]1[N:50]=[C:51]([NH:54][CH:55]=[O:56])[S:52][CH:53]=1)[C:23]([NH:25][CH:26]1[C:47](=[O:48])[N:28]2[C:29]([C:34]([O:36]CC3C=CC([N+]([O-])=O)=CC=3)=[O:35])=[C:30]([Cl:33])[CH2:31][S:32][C@H:27]12)=[O:24])=[O:18])([CH3:15])([CH3:14])[CH3:13]>[C].[Pd].O>[C:12]([O:16][C:17]([CH2:19][O:20][N:21]=[C:22]([C:49]1[N:50]=[C:51]([NH:54][CH:55]=[O:56])[S:52][CH:53]=1)[C:23]([NH:25][CH:26]1[C:47](=[O:48])[N:28]2[C:29]([C:34]([OH:36])=[O:35])=[C:30]([Cl:33])[CH2:31][S:32][C@H:27]12)=[O:24])=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 8028TetrahydrofuranHCID 131713137HCID 131713137, compound

Product 1

HCID 131713136HCID 131713136, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Procedure

Methanol (40 ml), tetrahydrofuran (20 ml) and acetic acid (0.3 ml) were added to 4-nitrobenzyl 7-[2-(tert-butoxycarbonylmethoxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 3.8 g). 10% Palladium carbon (1.9 g) containing water (3 ml) was added to the solution, and subjected to catalytic reduction for 4 hours. After removal of palladium carbon by filtration, the filtrate was concentrated in vacuo. To the residue were added ethyl acetate and water, and the solution was adjusted to pH 7.5 with a saturated solution of sodium bicarbonate. After the aqueous layer was separated, ethyl acetate was added to the aqueous layer, and adjusted to pH 2.0 with 10% hydrochloric acid. The ethyl acetate layer was separated. The organic solution was washed with a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with diisopropyl ether, and then the precipitates were collected by filtration and dried to give 7-[2-(tert-butoxycarbonylmethoxyimino)-2-(2-formamidothiazol- 4-yl)acetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 2.31 g).

Workup

  1. additionwas added to the solution
  2. customAfter removal of palladium carbon
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionTo the residue were added ethyl acetate and water
  6. customAfter the aqueous layer was separated
  7. additionethyl acetate was added to the aqueous layer
  8. customThe ethyl acetate layer was separated
  9. washThe organic solution was washed with a saturated solution of sodium chloride
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe residue was triturated with diisopropyl ether
  13. filtrationthe precipitates were collected by filtration
  14. customdried

Sources & evidence

ORD record
ord-7dc1174087ea4ee485046488d94a46dc
Source dataset
uspto-grants-1983_10
Patent number
US04409217

Reaction notes

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