Methanol → Diphenylmethyl 7-amino-3-[(2,5-bis(hydroxymethyl)-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylate

HRID 1032225Notes

Reaction equation

HRID 1032225 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]([CH2:20][OH:21])[N:19]=[C:15]4[N:14]=[C:13]([CH2:22][OH:23])[CH:12]=3)[CH2:7][S:8][C@H:3]12.CO.[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(=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:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:25])=[C:6]([CH2:9][S:10][C:11]3[N:16]4[N:17]=[C:18]([CH2:20][OH:21])[N:19]=[C:15]4[N:14]=[C:13]([CH2:22][OH:23])[CH:12]=3)[CH2:7][S:8][C@H:3]12

Participants

8

Reactant 4

HCID 887MethanolHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 79304DiphenylmethylidenehydrazineHCID 1317165527-Amino-3-[(2,5-bis(hydroxy-methyl)-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acid

Product 1

HCID 131716553Diphenylmethyl 7-amino-3-[(2,5-bis(hydroxymethyl)-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylate

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

In a suspension of 5.3 g of 7-amino-3-[(2,5-bis(hydroxymethyl)-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acid, 35 ml of methanol and 100 ml of methylene chloride was added dropwise, while stirring, diphenyldiazomethane synthesized from 6.9 g of benzophenonehydrazone, 7.6 g of mercuric oxide (yellow) and 70 ml of n-hexane, in 30 ml of methylene chloride solution, and the mixture was stirred at room temperature overnight. After the reaction mixture was condensed, ether was added thereto to crystalize, and crystal was collected by filtration and dried to obtain 7.28 g of the title compound.

Workup

  1. additionwas added dropwise
  2. stirringthe mixture was stirred at room temperature overnight
  3. additionwas added
  4. customto crystalize
  5. filtrationcrystal was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-04942a7a76f1483981131acc6657ff0d
Source dataset
uspto-grants-1990_09
Patent number
US04956462

Reaction notes

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