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

HRID 1032573Notes

Reaction equation

HRID 1032573 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]([CH2:20][OH:21])[N:19]=[C:15]4[N:14]=[C:13]([CH3:22])[CH:12]=3)[CH2:7][S:8][C@H:3]12.[C:28]1([C:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N+]=[N-])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=NN)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC>CO.C(Cl)Cl.CCOCC>[NH2:1][CH:2]1[C:26](=[O:27])[N:4]2[C:5]([C:23]([O:25][CH:34]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:24])=[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]([CH3:22])[CH:12]=3)[CH2:7][S:8][C@H:3]12

Participants

8

Reactant 4

HCID 8058HexaneHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 79304DiphenylmethylidenehydrazineHCID 1317165407-Amino-3-[(2-hydroxymethyl-5-methyl-s-triazolo[1,5-a]pyrimidin7-yl)thiomethyl]-3-cephem-4-carboxylic acid

Product 1

HCID 131716541Diphenylmethyl 7-amino-3-[(2-hydroxymethyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

In a suspension of 17.48 g of 7-amino-3-[(2-hydroxymethyl5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acid in 100 ml of methanol and 300 ml of methylene chloride was added dropwise diphenyldiazomethane as 50 ml of a methylene chloride solution, synthesized from 23.55 g of benzophenonehydrazone, 26 g of mercuric oxide (yellow) and 200 ml of n-hexane while stirring, and the mixture was stirred at room temperature overnight. After the reaction mixture was condensed, ether was added thereto to effect crystallization. The crystals thus formed were collected by filtration and dried to obtain 30.15 g of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. additionwas added
  3. customcrystallization
  4. customThe crystals thus formed
  5. filtrationwere collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c38b99b1d2484f52a940db0b3efe4c45
Source dataset
uspto-grants-1990_09
Patent number
US04958019

Reaction notes

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