Pyridine → HCID 178475883, compound

HRID 1904127Notes

Reaction equation

HRID 1904127 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[C:16]([NH:35][C:36]1[S:37][CH:38]=[C:39]([C:41](=[N:45][O:46][CH2:47][C:48]2[NH:52][N:51]=[N:50][N:49]=2)[C:42](O)=[O:43])[N:40]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH2:53][CH:54]1[C:73](=[O:74])[N:56]2[C:57]([C:66]([O:68][C:69]([CH3:72])([CH3:71])[CH3:70])=[O:67])=[C:58]([CH2:61][O:62][C:63](=[O:65])[CH3:64])[CH2:59][S:60][C@H:55]12.N1C=CC=CC=1>C(Cl)Cl.C(OCC)(=O)C>[C:63]([O:62][CH2:61][C:58]1[CH2:59][S:60][C@@H:55]2[CH:54]([NH:53][C:42](=[O:43])[C:41]([C:39]3[N:40]=[C:36]([NH:35][C:16]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[S:37][CH:38]=3)=[N:45][O:46][CH2:47][C:48]3[NH:52][N:51]=[N:50][N:49]=3)[C:73](=[O:74])[N:56]2[C:57]=1[C:66]([O:68][C:69]([CH3:70])([CH3:72])[CH3:71])=[O:67])(=[O:65])[CH3:64]

Participants

7

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 15573429t-Butyl 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylateHCID 178525937HCID 178525937, compound

Product 1

HCID 178475883HCID 178475883, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.5 g of dicyclohexylcarbodiimide in 5 ml of methylene chloride was added to a mixture of 1.024 g of the product of Step C, 0.656 mg of tert.-butyl 7-amino-3-acetoxymethyl-ceph-3-eme-4-carboxylate and 2 ml of pyridine and the mixture was stirred for one hour at room temperature. The mixture was vacuum filtered and 25 ml of N hydrochloric acid were added to the filtrate. The mixture was stirred for 5 minutes and the decanted organic phase was washed with 25 ml of water, was dried and evaporated to dryness under reduced pressure. The residue was taken up in isopropyl ether and efflorescenced. The mixture was vacuum filtered and the recovered product was rinsed with isopropyl ether and dried to obtain 1.778 g of raw product. The latter was dissolved in 4 ml of ethyl acetate and the solution was treated with activated carbon and was filtered. 20 ml of isopropyl ether were added to the filtrate over 5 minutes with stirring and after stirring for another 5 minutes, the mixture was vacuum filtered. The recovered product was rinsed with isopropyl ether and dried to obtain 1.412 g of the syn isomer of tert.-butyl 3-acetoxymethyl-7-[2-(2-tritylamino-4-thiazolyl)-2-(tetrazol-5-yl-methyloxyimino)-acetamido]-ceph-3-eme-4-carboxylate in the form of a white product melting at 158° C.

Workup

  1. filtrationfiltered
  2. addition25 ml of N hydrochloric acid were added to the filtrate
  3. stirringThe mixture was stirred for 5 minutes
  4. washthe decanted organic phase was washed with 25 ml of water
  5. customwas dried
  6. customevaporated to dryness under reduced pressure
  7. filtrationfiltered
  8. washthe recovered product was rinsed with isopropyl ether
  9. customdried
  10. customto obtain 1.778 g of raw product
  11. additionthe solution was treated with activated carbon
  12. filtrationwas filtered
  13. addition20 ml of isopropyl ether were added to the filtrate over 5 minutes
  14. stirringwith stirring
  15. stirringafter stirring for another 5 minutes
  16. filtrationfiltered
  17. washThe recovered product was rinsed with isopropyl ether
  18. customdried

Sources & evidence

ORD record
ord-788ea931844f43d5a6a62f5ddb655530
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

Loading…