Methanesulfonic Acid → (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-[[5-(3,4-dihydroxyphenyl)-2-phenylpyrimidin-4-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755853Notes

Reaction equation

HRID 1755853 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[C:30]([C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([OH:38])[CH:32]=4)=[CH:29][N:28]=[C:27]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[N:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1.[NH2:46][O:47][CH2:48][C:49]1[NH:50][CH:51]=[C:52]([OH:56])[C:53](=[O:55])[N:54]=1.CS(O)(=O)=O>CC(N(C)C)=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:46]/[O:47][CH2:48][C:49]2[NH:50][CH:51]=[C:52]([OH:56])[C:53](=[O:55])[N:54]=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[C:30]([C:31]4[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([OH:38])[CH:32]=4)=[CH:29][N:28]=[C:27]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[N:26]=2)=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 86748843(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[(5-(3,4-dihydroxyphenyl)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 178514652HCID 178514652, compound

Product 1

HCID 178508506(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-[[5-(3,4-dihydroxyphenyl)-2-phenylpyrimidin-4-yl]sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidYield 36%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

(6R,7R)-7-(2-Amino-4-thiazoleglyoxylamido)-3-[[(5-(3,4-dihydroxyphenyl)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (60 mg) (0.09 mmol), 20.5 mg (0.13 mmol) of 2-(aminooxy)methyl-5-hydroxy-4(1H)-pyrimidinone and 13 mg (0.13 mmol) of methanesulphonic acid are dissolved in 0.6 ml of absolute dimethylacetamide. After stirring at room temperature for 18 hours the mixture is concentrated in a high vacuum at room temperature and the residue is crystallized using ethanol. The product is washed with diethyl ether and dried in a high vacuum at room temperature. There are obtained 26 mg of (6R,7R)-7-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyrimidinyl)methoxy]imino]acetamido]-3-[[[5-(3,4-dihydroxyphenyl)-2-phenyl-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2 -carboxylic acid as a yellow powder. A further 28 mg of yellow crystals of the same compound can be obtained from the mother liquor after concentration.

Workup

  1. concentrationis concentrated in a high vacuum at room temperature
  2. customthe residue is crystallized
  3. washThe product is washed with diethyl ether
  4. customdried in a high vacuum at room temperature

Sources & evidence

ORD record
ord-6190a668f3a84969bab460f36f0ab08a
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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