Diethyl Ether → Cefuroxime

HRID 894836Notes

Reaction equation

HRID 894836 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[N:24]/[O:25][CH3:26])/[C:7]([NH:9][C@@H:10]1[C:22](=[O:23])[N:12]2[C:13]([C:19]([OH:21])=[O:20])=[C:14]([CH2:17][OH:18])[CH2:15][S:16][C@H:11]12)=[O:8].[N-:27]=[C:28]=[O:29].C([O-])(O)=O.[Na+].CCOCC>O1CCOCC1>[CH3:26][O:25]/[N:24]=[C:6](\[C:7]([NH:9][C@@H:10]1[C:22](=[O:23])[N:12]2[C:13]([C:19]([OH:21])=[O:20])=[C:14]([CH2:17][O:18][C:28]([NH2:27])=[O:29])[CH2:15][S:16][C@H:11]12)=[O:8])/[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 105034IsocyanateHCID 516892Sodium Bicarbonate2×HCID 9800056(6R,7R)-7-(((2Z)-2-(2-Furanyl)-2-(methoxyimino)acetyl)amino)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid

Product 1

HCID 5479529Cefuroxime

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (6R,7R)-7-[Z-2-(fur-2-yl)-2-methoxyiminoacetamido]-3-hydroxymethylceph-3-em-4carboxylic acid (3.8 g) in dioxan (35 ml) was added to the above isocyanate reagent in one portion and the resulting solution was stirred at ca 22° for 7 minutes. The reaction mixture was poured into 3% aqueous NaHCO3 solution (170 ml) and the pH was adjusted to 5 by the addition of more aqueous NaHCO3 solution. After heating to 40° for 2 hours and allowing to cool to 22° over 14 hours, the reaction mixture was washed (at pH 5.9) with ethyl acetate (2×200 ml), the aqueous layer was separated, layered with ethyl acetate (200 ml), and acidified with concentrated hydrochloric acid to pH 1.9. The organic layer was separated and the aqueous layer re-extracted with ethyl acetate (200 ml). The organic extracts were combined, washed with brine (2×400 ml), dried (MgSO4) and evaporated to give a white solid which, on trituration with ether (100 ml) afforded the title compound (3.18 g, 75% m.p. (MSO2) 175°; [α]D +42° (c 1.02, DMSO).

Workup

  1. temperatureAfter heating to 40° for 2 hours
  2. temperatureto cool to 22° over 14 hours
  3. washthe reaction mixture was washed (at pH 5.9) with ethyl acetate (2×200 ml)
  4. customthe aqueous layer was separated
  5. customThe organic layer was separated
  6. extractionthe aqueous layer re-extracted with ethyl acetate (200 ml)
  7. washwashed with brine (2×400 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a white solid which

Sources & evidence

ORD record
ord-de7698298c374395b12529ce325f21f7
Source dataset
uspto-grants-1981_08
Patent number
US04284767

Reaction notes

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