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

HRID 1032213Notes

Reaction equation

HRID 1032213 reaction equation
[NH2:1][CH:2]1[C:28](=[O:29])[N:4]2[C:5]([C:25]([OH:27])=[O:26])=[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]([C:22]([OH:24])=[O:23])[CH:12]=3)[CH2:7][S:8][C@H:3]12.CO.[C:32]1([C:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[N+]=[N-])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(=NN)(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl.CCOCC.CCCCCC>[NH2:1][CH:2]1[C:28](=[O:29])[N:4]2[C:5]([C:25]([O:27][CH:38]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:26])=[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]([C:22]([OH:24])=[O: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 1317165467-Amino-3-[(5-carboxy-2-hydroxymethyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylic acid

Product 1

HCID 131716547Diphenylmethyl 7-amino-3-[(5-carboxy-2-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

To a suspension of 10 g of 7-amino-3-[(5-carboxy-2-hydroxymethyl-s-triazolo[1,5-a]pyrimidin-7yl)thiomethyl]-3-cephem-4-carboxylic acid, 100 ml of methanol and 300 ml of methylene chloride was added dropwise while stirring diphenyldiazomethane, which had been synthesized from 19.6 g of benzophenonehydrazone, 21.6 g of mercuric oxide (yellow) and 150 ml of n-hexane, in 30 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 to obtain 13.9 g of the title compound.

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. customcrystallization
  4. filtrationThe crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-7ddcc59179314eec9144e7af8491cb7f
Source dataset
uspto-grants-1990_09
Patent number
US04956462

Reaction notes

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