Tributylamine → HCID 131709954, compound

HRID 1580514Notes

Reaction equation

HRID 1580514 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:23][C:8]([CH2:9][C:10]2[CH2:11][S:12][C@@H:13]3[CH:20](N)[C:19](=[O:22])[N:14]3[C:15]=2[C:16]([OH:18])=[O:17])=[CH:7][CH:6]=1)=[O:4].C([N:28](CCCC)CCCC)CCC.[Cl:37][CH2:38][CH2:39][N:40]=[C:41]=[O:42]>CN(C)C=O>[Cl:37][CH2:38][CH2:39][NH:40][C:41]([C@@H:20]1[C:19](=[O:22])[N:14]2[C:15]([C:16]([OH:18])=[O:17])=[C:10]([CH2:9][C:8]3[O:23][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)[CH:11]([NH2:28])[S:12][C@H:13]12)=[O:42]

Participants

5

Reactant 3

HCID 7622TributylamineHCID 160352-Chloroethyl isocyanateHCID 68134122HCID 68134122, compound

Product 1

HCID 131709954HCID 131709954, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 10% suspension of 0.100 g of 3-(5-methoxycarbonyl-furfuryl)-7-amino-ceph-3-em-4-carboxylic acid and 0.0644 g of tri-n-butylamine in absolute dimethylformamide is treated with a 5% solution of 0.0633 g of 2-chloroethylisocyanate. The reaction mixture is vibrated in an ultrasonics bath for 90 minutes at room temperature. The yellowish brown reaction solution is evaporated to dryness under a high vacuum and the residue is partitioned several times between 25 ml of a 0.5 molar aqueous dipotassium hydrogen phosphate solution and 10 ml of ethyl acetate. The aqueous extracts are covered with fresh ethyl acetate, acidified to pH 2 by dropwise addition of 5-molar aqueous phosphoric acid and extracted with three portions of ethyl acetate. The organic extracts are washed with water, dried over anhydrous magnesium sulphate and evaporated under reduced pressure. The residue is placed onto preparative thin-layer plates (silica gel, with fluorescence indicator). The plates are developed during approximately 5 hours in the system n-butanol/glacial acetic acid/water (44:12:44). After drying, the main band absorbing ultraviolet light (λ = 254 mμ) is scraped from the plates and extracted several times with acetone. The extracts are filtered through a filter having a diatomaceous earth preparation as filter auxiliary and evaporated to dryness. The 7β-(2-chloroethylamino-carbonyl)-amino-3-(5-methoxycarbonyl-furfuryl)-ceph-3-em-4-carboxylic acid is obtained in the form of a glassy, colourless residue; ultraviolet absorption spectrum (95% aqueous ethanol): λmax = 269 mμ (ε = 22100).

Workup

  1. customThe yellowish brown reaction solution is evaporated to dryness under a high vacuum
  2. customthe residue is partitioned several times between 25 ml of a 0.5 molar aqueous dipotassium hydrogen phosphate solution and 10 ml of ethyl acetate
  3. additionacidified to pH 2 by dropwise addition of 5-molar aqueous phosphoric acid
  4. extractionextracted with three portions of ethyl acetate
  5. washThe organic extracts are washed with water
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated under reduced pressure
  8. waitThe plates are developed during approximately 5 hours in the system n-butanol/glacial acetic acid/water (44:12:44)
  9. customAfter drying
  10. customthe main band absorbing ultraviolet light (λ = 254 mμ)
  11. extractionextracted several times with acetone
  12. filtrationThe extracts are filtered through a filter
  13. customa diatomaceous earth preparation
  14. filtrationas filter auxiliary
  15. customevaporated to dryness

Sources & evidence

ORD record
ord-8fbd2d051630438998b5f60ab36138ec
Source dataset
uspto-grants-1976_01
Patent number
US03932465

Reaction notes

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