p-Toluenesulfonic acid monohydrate → 3-[[[2-Carbamoyl-5-methyl-s-triazolo[1,5-a]-pyrimidin-7-yl) thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 345172Notes

Reaction equation

HRID 345172 reaction equation
NC1SC=C(C(=O)C(N[C@@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[S:13][CH2:14][C:15]([CH2:23][S:24][C:25]2[N:30]4[N:31]=[C:32]([C:34](=[O:36])[NH2:35])[N:33]=[C:29]4[N:28]=[C:27]([CH3:37])[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=O)N=1.NOC(C)(C)C(NNC(C1NC=C(O)C(=O)C=1)=O)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(N(C)C)=O>[C:34]([C:32]1[N:33]=[C:29]2[N:28]=[C:27]([CH3:37])[CH:26]=[C:25]([S:24][CH2:23][C:15]3[CH2:14][S:13][CH:12]4[N:17]([C:18](=[O:19])[CH2:11]4)[C:16]=3[C:20]([OH:22])=[O:21])[N:30]2[N:31]=1)(=[O:36])[NH2:35]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 199939031-[2-(Aminooxy)-2-methylpropionyl]-2-[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridyl)carbonyl]hydrazineHCID 86744944(6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[(2-carbamoyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 199939003-[[[2-Carbamoyl-5-methyl-s-triazolo[1,5-a]-pyrimidin-7-yl) thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

0.228 g (0.4 mmol) of (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[(2-carbamoyl -5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo [4.2.0]oct-2-ene-2-carboxylic acid was dissolved in 2 ml of dimethylacetamide. 0.140 g (0.52 mmol) of 1-[2-(aminooxy)-2-methylpropionyl]-2-[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridyl) carbonyl]hydrazine and 0.100 g (0.52 mmol) of p-toluenesulfonic acid hydrate were added. After stirring for 20 hours at room temperature the dimethylacetamide was evaporated off at strongly reduced pressure and the residue was taken up in water and stirred for 15 minutes in order to completely precipitate the product. The product was filtered off, washed well with water and dried under strongly reduced pressure at room temperature. (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[1,4-dihydro-5-hydroxy -4-oxo-2-pyridyl)carbonyl]carbazoyl]-1-methylethoxy]imino] -acetamido]-3-[[[2-carbamoyl-5-methyl-s-triazolo[1,5-a]-pyrimidin-7-yl) thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid was obtained as beige-colored powder.

Workup

  1. customwas evaporated off at strongly reduced pressure
  2. customto completely precipitate the product
  3. filtrationThe product was filtered off
  4. washwashed well with water
  5. customdried under strongly reduced pressure at room temperature

Sources & evidence

ORD record
ord-0957e77b73c54ee08d23b4631afce85a
Source dataset
uspto-grants-1991_10
Patent number
US05055572

Reaction notes

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