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

HRID 1032219Notes

Reaction equation

HRID 1032219 reaction equation
[NH2:1][CH:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([OH:25])=[O:24])=[C:6]([CH2:9][S:10][C:11]3[N:16]4[N:17]=[C:18]([CH3:20])[N:19]=[C:15]4[N:14]=[C:13]([CH2:21][OH:22])[CH:12]=3)[CH2:7][S:8][C@H:3]12.CO.[C:30]1([C:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N+]=[N-])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(=NN)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl.CCOCC.CCCCCC>[NH2:1][CH:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([O:25][CH:36]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[O:24])=[C:6]([CH2:9][S:10][C:11]3[N:16]4[N:17]=[C:18]([CH3:20])[N:19]=[C:15]4[N:14]=[C:13]([CH2:21][OH: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 1317165487-Amino-3-[(5-hydroxymethyl2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acid

Product 1

HCID 131716549Diphenylmethyl 7-amino-3-[(5-hydroxymethyl-2-methyl-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 11.6 g of 7-amino-3-[(5-hydroxymethyl-2-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acid, 70 ml of methanol and 200 ml of methylene chloride was added dropwise, while stirring, diphenyldiazomethane synthesized from 15.7 g of benzophenonehydrazone, 17.3 g of mercuric oxide (yellow) and 130 ml of n-hexane, in 50 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 15.9 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-064fff0b9ad54b6a888ca48a4797b4d5
Source dataset
uspto-grants-1990_09
Patent number
US04956462

Reaction notes

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