Pyridine → HCID 131713460, compound

HRID 1904131Notes

Reaction equation

HRID 1904131 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][C:33]([NH2:35])=[S:34])[C:27]([OH:29])=O)[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:42][C:43]([O:45][CH2:46][C:47]1[CH2:56][S:55][C@@H:50]2[C@H:51]([NH2:54])[C:52](=[O:53])[N:49]2[C:48]=1[C:57]([OH:59])=[O:58])=[O:44]>C(Cl)Cl>[C:43]([O:45][CH2:46][C:47]1[CH2:56][S:55][C@@H:50]2[CH:51]([NH:54][C:27](=[O:29])[C:26]([C:24]3[N:25]=[C:21]([NH:20][C:1]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[S:22][CH:23]=3)=[N:30][O:31][CH2:32][C:33]([NH2:35])=[S:34])[C:52](=[O:53])[N:49]2[C:48]=1[C:57]([OH:59])=[O:58])(=[O:44])[CH3:42]

Participants

5

Reactant 3

HCID 1049PyridineHCID 4413287-Aminocephalosporanic acidHCID 53800103HCID 53800103, compound

Product 1

HCID 131713460HCID 131713460, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.5 g of dicyclohexyldicarbodiimide in 5 ml of methylene chloride was added to a solution of 1.01 g of the product of Step A, 2 ml of pyridine and 0.656 g of 7-amino-cephalosporanic acid and the mixture was stirred at room temperature to effect precipitation and was vacuum filtered. The product was rinsed with methylene chloride and dried to remove about 0.5 g of dicyclohexylurea. The filtrate was poured into 25 ml of hydrochloric acid and the mixture was stirred for 5 minutes. The decanted organic phase was washed with 25 ml of water and was dried and vacuum filtered. The filtrate was evaporated to dryness and the residue was taken up in isopropyl ether. Efflorescence occured and the mixture was vacuum filtered. The recovered product was rinsed and was dissolved in 4 ml of ethyl acetate 0.18 g of activated carbon were added thereto and the mixture was vacuum filtered. The filter was rinsed with ethyl acetate and the filtrate was stirred while 20 ml of isopropyl ether were added over 5 minutes. The mixture was stirred another 5 minutes and was vacuum filtered. The recovered product was rinsed with isopropyl ether and was dried to obtain the syn isomer of 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(2-amino-2-thioxoethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. customprecipitation
  2. filtrationfiltered
  3. washThe product was rinsed with methylene chloride
  4. customdried
  5. customto remove about 0.5 g of dicyclohexylurea
  6. additionThe filtrate was poured into 25 ml of hydrochloric acid
  7. stirringthe mixture was stirred for 5 minutes
  8. washThe decanted organic phase was washed with 25 ml of water
  9. customwas dried
  10. filtrationvacuum filtered
  11. customThe filtrate was evaporated to dryness
  12. filtrationfiltered
  13. washThe recovered product was rinsed
  14. dissolutionwas dissolved in 4 ml of ethyl acetate 0.18 g of activated carbon
  15. additionwere added
  16. filtrationfiltered
  17. washThe filter was rinsed with ethyl acetate
  18. stirringthe filtrate was stirred while 20 ml of isopropyl ether
  19. additionwere added over 5 minutes
  20. stirringThe mixture was stirred another 5 minutes
  21. filtrationfiltered
  22. washThe recovered product was rinsed with isopropyl ether
  23. customwas dried

Sources & evidence

ORD record
ord-754b7d9275004923b4bbf94a5d5a6d03
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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