Dicyclohexylcarbodiimide → HCID 131716561, compound

HRID 1032229Notes

Reaction equation

HRID 1032229 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10]([OH:12])=O)[N:8]=1)=O.[NH2:16][CH:17]1[C:50](=[O:51])[N:19]2[C:20]([C:39]([O:41][CH2:42][O:43][C:44](=[O:49])[C:45]([CH3:48])([CH3:47])[CH3:46])=[O:40])=[C:21]([CH2:24][S:25][C:26]3[N:31]4[N:32]=[C:33]([CH2:35][O:36][CH3:37])[N:34]=[C:30]4[N:29]=[C:28]([CH3:38])[CH:27]=3)[CH2:22][S:23][C@H:18]12.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1.P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>CN(C=O)C.CCOCC.C(OCC)(=O)C.O.CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH3:15])[C:10]([NH:16][CH:17]2[C:50](=[O:51])[N:19]3[C:20]([C:39]([O:41][CH2:42][O:43][C:44](=[O:49])[C:45]([CH3:46])([CH3:48])[CH3:47])=[O:40])=[C:21]([CH2:24][S:25][C:26]4[N:31]5[N:32]=[C:33]([CH2:35][O:36][CH3:37])[N:34]=[C:30]5[N:29]=[C:28]([CH3:38])[CH:27]=4)[CH2:22][S:23][C@H:18]23)=[O:12])[N:8]=1

Participants

12

Reactant 6

HCID 10868DicyclohexylcarbodiimideHCID 24813Phosphorus oxychlorideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27245112-(2-Formylamino-1,3-Thiazol-4-Yl)-2-(Methoxyimino)Acetic AcidHCID 131716560HCID 131716560, compound

Product 1

HCID 131716561HCID 131716561, compoundYield 31.6%

Reagents, catalysts & solvents 5

HCID 887MethanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 50 ml of DMF were added 3.43 g of 2-(2-formylamino1,3-thiazol-4-yl)-2-methoxyiminoacetic acid, 10.1 g of pivaloyloxymethyl 7-amino-3-[(2-methoxymethyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylate and 2.76 g of 1-hydroxybenzotriazole and ice-cooled, and 3.71 g of DCC was added to the solution and the mixture was stirred for 1.5 hours under ice-cooling. After filtration of the reaction mixture, 20 ml of chloroform was added to the filtrate, and the mixture was added dropwise into 4 liters of ether. Precipitates were collected by filtration and dried to obtain a powder. To 1.57 ml of phosphorus oxychloride was added 80 ml of ice-cooled methanol, and the powder previously obtained was added thereto and the mixture was stirred for 1.5 hours under ice-cooling. After the mixture was condensed to a half, the residue was added dropwise to a mixed solution of 200 ml of water and 200 ml of ethyl acetate and the mixture was neutralized with addition of sodium hydrogencarbonate. An organic layer was separated, washed with water and then dried over anhydrous magnesium sulfate, followed by evaporation of a solvent to obtain an oily product. The oily product was purified through silica gel column chromatography. To the oily product obtained was added ether to powderize, and it was collected by filtration and dried to obtain 3.4 g of the title compound.

Workup

  1. temperaturecooled
  2. temperaturecooling
  3. filtrationAfter filtration of the reaction mixture, 20 ml of chloroform
  4. additionwas added to the filtrate
  5. additionthe mixture was added dropwise into 4 liters of ether
  6. customPrecipitates
  7. filtrationwere collected by filtration
  8. customdried
  9. customto obtain a powder
  10. customthe powder previously obtained
  11. additionwas added
  12. stirringthe mixture was stirred for 1.5 hours under ice-
  13. temperaturecooling
  14. customcondensed to a half
  15. customAn organic layer was separated
  16. washwashed with water
  17. dry with materialdried over anhydrous magnesium sulfate
  18. customfollowed by evaporation of a solvent
  19. customto obtain an oily product
  20. customThe oily product was purified through silica gel column chromatography
  21. customTo the oily product obtained
  22. filtrationit was collected by filtration
  23. customdried

Sources & evidence

ORD record
ord-c19a4ef78c924b88b152b3c3ab86c4de
Source dataset
uspto-grants-1990_09
Patent number
US04956462

Reaction notes

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