p-Toluenesulfonic acid monohydrate → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(5-hydroxy-6-oxo-1H-pyrimidin-2-yl)methoxyimino]acetyl]amino]-3-[(2-carbamoyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 345175Notes

Reaction equation

HRID 345175 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=O)[C:8]([NH:10][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:9])[N:6]=1.[NH2:39][O:40][CH2:41][C:42]1[NH:43][CH:44]=[C:45]([OH:49])[C:46](=[O:48])[N:47]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:39]/[O:40][CH2:41][C:42]2[NH:43][CH:44]=[C:45]([OH:49])[C:46](=[O:48])[N:47]=2)/[C:8]([NH:10][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:9])[N:6]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 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 acidHCID 178514652HCID 178514652, compound

Product 1

HCID 178429668(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(5-hydroxy-6-oxo-1H-pyrimidin-2-yl)methoxyimino]acetyl]amino]-3-[(2-carbamoyl-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

0.230 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 3.5 ml of dimethylacetamide. Within 6 hours 0.11 g (0.7 mmol) of 2-(aminooxy)methyl-5-hydroxy-4(1H)-pyrimidinone and 0.133 g (0.7 mmol) of p-toluenesulfonic acid hydrate were added. After further stirring for 18 hours the dimethylacetamide was evaporated off at strongly reduced pressure, and the residue was taken up in water and stirred for 20 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-pyrimidinyl) methoxy]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 a beige 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-d9fbf266f0c14e92bb2326654bb5de85
Source dataset
uspto-grants-1991_10
Patent number
US05055572

Reaction notes

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