Formamide → HCID 131713362, compound

HRID 2295935Notes

Reaction equation

HRID 2295935 reaction equation
[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH2:16])[C:14](=[O:17])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])=[N+:2]=[N-:3].C(N)=O.C1N2CCN(CC2)C1.I.N1C=CC=CC=1.[C:36]([NH:55][C:56]1[S:57][CH:58]=[C:59]([C:61](=[N:65][O:66][CH2:67][CH2:68][S:69][CH:70]=[N:71][NH2:72])[C:62](O)=[O:63])[N:60]=1)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl.CN(C)C=O>[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:62](=[O:63])[C:61]([C:59]3[N:60]=[C:56]([NH:55][C:36]([C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[S:57][CH:58]=3)=[N:65][O:66][CH2:67][CH2:68][S:69][CH:70]=[N:71][NH2:72])[C:14](=[O:17])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])=[N+:2]=[N-:3]

Participants

9

Reactant 6

HCID 713FormamideHCID 9237DabcoHCID 10868DicyclohexylcarbodiimideHCID 31273118820-83-22×HCID 128022197-Amino-3-azidomethyl-3-cephem-4-carboxylic acidHCID 54325691HCID 54325691, compound

Product 1

HCID 131713362HCID 131713362, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
15 °C

Procedure

A mixture of 255 mg of 3-azidomethyl-7-amino-ceph-3-eme-4-carboxylic acid and 3 ml of anhydrous formamide was stirred for 15 minutes and then 168 mg of triethylenediamine were added in fractions. 412 mg of pyridine hydroiodide were added to the resulting solution and after cooling the mixture to 15° C., 532 mg of 2-(2-tritylamino-4-thiazolyl)-2-(2-aminoiminomethylthioethoxyimino)-acetic acid, 207 mg of pyridine hydroiodide and 3 ml of dimethylformamide were added all at once to the mixture. 412 mg of dicyclohexylcarbodiimide were added to the mixture which was stirred at 15° C. for 20 minutes, at 20° C. for 40 minutes and was then vacuum filtered. 100 ml of water were added to the filtrate and the mixture was stirred for 30 minutes, let stand for 30 minutes and was then vacuum filtered. The recovered product was washed with water and dried to obtain 437 mg of raw product which was stirred with 8.6 ml of chloroform for 30 minutes. The mixture was vacuum filtered and the filtrate was treated with activated carbon and was vacuum filtered. The filtrate was evaporated to dryness to obtain 350 mg of internal salt of syn isomer of 3-azidomethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(2-aminoiminomethylthioethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. stirringwas stirred at 15° C. for 20 minutes, at 20° C. for 40 minutes
  2. filtrationvacuum filtered
  3. addition100 ml of water were added to the filtrate
  4. stirringthe mixture was stirred for 30 minutes
  5. waitlet stand for 30 minutes
  6. filtrationvacuum filtered
  7. washThe recovered product was washed with water
  8. customdried
  9. customto obtain 437 mg of raw product which
  10. filtrationfiltered
  11. additionthe filtrate was treated with activated carbon
  12. filtrationfiltered
  13. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-580a73381dce431f8ae332751e5ead30
Source dataset
uspto-grants-1984_01
Patent number
US04426519

Reaction notes

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