Isocyanate → Cefuroxime

HRID 894837Notes

Reaction equation

HRID 894837 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]>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

4

Reactant 2

HCID 105034IsocyanateHCID 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 5479529CefuroximeYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (6R,7R)-7-[Z-2-(fur-2-yl)-2-methoxyiminoacetamido]-3-hydroxymethyl-ceph-3-em-4-carboxylic acid (3.84 g) in dioxan (35 ml) was added to the above isocyanate solution at ca 25°. The reaction and work up was similar to that described in Example 8, except that the product was not triturated with ether, and yielded the title compound as a pale yellow solid, (3.28 g, 77%) m.p. (M802)179°; [α]D22 +54.4° (c.1.0, DMSO).

Workup

  1. customThe reaction
  2. customwas not triturated with ether

Sources & evidence

ORD record
ord-02c6842c160c4ee2b1af827e02ee09dc
Source dataset
uspto-grants-1981_08
Patent number
US04284767

Reaction notes

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