Trichloroacetyl isocyanate → Cefuroxime Sodium

HRID 1277520Notes

Reaction equation

HRID 1277520 reaction equation
ClC(Cl)(Cl)[C:3]([N:5]=C=O)=[O:4].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1/[C:15](=[N:33]/[O:34][CH3:35])/[C:16]([NH:18][C@@H:19]1[C:31](=[O:32])[N:21]2[C:22]([C:28]([OH:30])=[O:29])=[C:23]([CH2:26][OH:27])[CH2:24][S:25][C@H:20]12)=[O:17].C(C(CCCC)C([O-])=O)C.[Na+:46]>CO.C1COCC1.ClCCl>[CH3:35][O:34]/[N:33]=[C:15](\[C:16]([NH:18][C@@H:19]1[C:31](=[O:32])[N:21]2[C:22]([C:28]([O-:30])=[O:29])=[C:23]([CH2:26][O:27][C:3]([NH2:5])=[O:4])[CH2:24][S:25][C@H:20]12)=[O:17])/[C:11]1[O:10][CH:14]=[CH:13][CH:12]=1.[Na+:46]

Participants

7

Reactant 3

HCID 76400Trichloroacetyl isocyanateHCID 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 acidHCID 23672331Sodium 2-ethylhexanoate

Product 1

HCID 23670318Cefuroxime Sodium

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of THF (130 ml), dichloromethane (45 ml), and trichloroacetyl isocyanate (9.3 ml) was protected from moisture and cooled to -10°.To the stirred mixture was added (6R,7R)-7-[Z-2-(fur-2-yl)-2-methoxyiminoacetamido]-3-hydroxymethylceph-3-em-4-carboxylic acid (20 g) in one charge followed by THF (40 ml). The mixture was stirred for 10 minutes at 0° to +5° and then warmed to 22° , There was then added, in one charge, a solution of sodium 2-ethylhexanoate (20 g) in methanol (40 ml) and, after stirring for1 minute, the mixture was left undisturbed at 25° for 2 hours to crystallise. The crystalline material was collected by filtration, washed with ethanol (2×100 ml), and dried in vacuo at 35° to give sodium cefuroxime (24.1 g). The isolated product was shown by G.L.C. to contain 5.3% w/w of ethanol, 0.6% w/w of THF, and 0.04% w/w of methanol.

Workup

  1. temperaturecooled to -10°
  2. additioncharge
  3. temperaturewarmed to 22°
  4. additionThere was then added, in one
  5. additioncharge
  6. waitthe mixture was left undisturbed at 25° for 2 hours
  7. customto crystallise
  8. filtrationThe crystalline material was collected by filtration
  9. washwashed with ethanol (2×100 ml)
  10. customdried in vacuo at 35°

Sources & evidence

ORD record
ord-fa318ea9815c4123a8c1572fafe4a7a0
Source dataset
uspto-grants-1981_07
Patent number
US04277601

Reaction notes

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