2-[(aminooxy)methyl]-5-hydroxy-4H-pyran-4-one p-toluenesulphonate → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(5-hydroxy-4-oxopyran-2-yl)methoxyimino]acetyl]amino]-3-[[5-(3,4-dihydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755842Notes

Reaction equation

HRID 1755842 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]=[CH:32][CH:33]=[C:29]4[N:28]=[C:27]([C:34]4[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([OH:41])[CH:35]=4)[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:54][O:55][CH2:56][C:57]1[O:58][CH:59]=[C:60]([OH:64])[C:61](=[O:63])[CH:62]=1>>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:54]/[O:55][CH2:56][C:57]2[O:58][CH:59]=[C:60]([OH:64])[C:61](=[O:63])[CH:62]=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]=[CH:32][CH:33]=[C:29]4[N:28]=[C:27]([C:34]4[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([OH:41])[CH:35]=4)[CH:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1

Participants

3

Reactant 2

HCID 199178712-[(aminooxy)methyl]-5-hydroxy-4H-pyran-4-one p-toluenesulphonateHCID 136401246(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)pyrazolo[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 136464596(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(5-hydroxy-4-oxopyran-2-yl)methoxyimino]acetyl]amino]-3-[[5-(3,4-dihydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 92.2%

Procedure

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (59 mg) (0.095 mmol) and 41 mg (0.121 mmol) of 2-[(aminooxy)methyl]-5-hydroxy-4H-pyran-4-one p-toluenesulphonate (1:1) are dissolved in 2 ml of absolute dimethylaeetamide. After stirring at room temperature for 24 hours the solvent is removed and the residue is treated with 4 ml of water. The precipitated product is filtered off and washed with water. After drying in a high vacuum at room temperature there are obtained 67 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(5-hydroxy-4-oxo-4 H-pyran-2-yl)methoxy]imino]acetamido]-3-[[[5-(3,4-dihydroxyphenyl)pyrazolo[1,5-a]pyrimidin-7-yl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a yellow powder.

Workup

  1. customis removed
  2. additionthe residue is treated with 4 ml of water
  3. filtrationThe precipitated product is filtered off
  4. washwashed with water
  5. customAfter drying in a high vacuum at room temperature

Sources & evidence

ORD record
ord-828ff4db580b4c34b769add522dd72a9
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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