Methanol → HCID 131716545, compound

HRID 1032580Notes

Reaction equation

HRID 1032580 reaction equation
[NH2:1][CH:2]1[C:27](=[O:28])[N:4]2[C:5]([C:24]([OH:26])=[O:25])=[C:6]([CH2:9][S:10][C:11]3[N:16]4[N:17]=[C:18](OC)[N:19]=[C:15]4[N:14]=[C:13]([CH3:22])[C:12]=3C)[CH2:7][S:8][C@H:3]12.[CH3:29][OH:30].[C:31]1([C:37]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)=[N+]=[N-])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[C:46](=NN)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl.CCOCC.CCCCCC>[NH2:1][CH:2]1[C:27](=[O:28])[N:4]2[C:5]([C:24]([O:26][CH:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:25])=[C:6]([CH2:9][S:10][C:11]3[N:16]4[N:17]=[C:18]([CH2:29][O:30][CH3:46])[N:19]=[C:15]4[N:14]=[C:13]([CH3:22])[CH:12]=3)[CH2:7][S:8][C@H:3]12

Participants

8

Reactant 4

HCID 887MethanolHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 79304DiphenylmethylidenehydrazineHCID 131716581HCID 131716581, compound

Product 1

HCID 131716545HCID 131716545, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

To a suspension comprising 30 g of 7-amino-3-[(2-methoxy- methyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thio -methyl]-3-cephem-4-carboxylic acid, 170 ml of methanol and 510 ml of methylene chloride was added dropwise while stirring diphenyldiazomethane, which had been synthesized from 39.25 g of benzophenonehydrazone, 43.22 g of mercuric oxide (yellow) and 350 ml of n-hexane, in 50 ml of methylene chloride, and the mixture was stirred at room temperature overnight. After the reaction mixture was condensed and ether was added thereto to effect crystallization. The crystals were collected by filtration and dried, and the resulting powder was purified through silica gel column chromatography to obtain 31.1 g of the title compound.

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. customcrystallization
  4. filtrationThe crystals were collected by filtration
  5. customdried
  6. customthe resulting powder was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-66479983445d41ce803c6a2f9158aac0
Source dataset
uspto-grants-1990_09
Patent number
US04958019

Reaction notes

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