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

HRID 704509Notes

Reaction equation

HRID 704509 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-hydroxymethyl2-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 crystallize, 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 crystallize
  5. filtrationcrystal was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-a8266739166a459eb5cb44c523bc602b
Source dataset
uspto-grants-1991_01
Patent number
US04987129

Reaction notes

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