Acetonitrile → (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

HRID 1755852Notes

Reaction equation

HRID 1755852 reaction equation
[NH2:1][C@@H:2]1[C:9](=[O:10])[N:8]2[C@@H:3]1[S:4][CH2:5][C:6]([CH2:14][S:15][C:16]1[C:21]([C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([OH:29])[CH:23]=3)=[CH:20][N:19]=[C:18]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:17]=1)=[C:7]2[C:11]([OH:13])=[O:12].[OH-:36].[K+].[C:38](#[N:40])[CH3:39]>O>[NH2:8][C:3]1[S:4][CH:39]=[C:38]([C:9](=[O:10])[C:2]([NH:1][C@@H:2]2[C:9](=[O:10])[N:8]3[C@@H:3]2[S:4][CH2:5][C:6]([CH2:14][S:15][C:16]2[C:21]([C:22]4[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([OH:29])[CH:23]=4)=[CH:20][N:19]=[C:18]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:17]=2)=[C:7]3[C:11]([OH:13])=[O:12])=[O:36])[N:40]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14797Potassium HydroxideHCID 54291490(6R,7R)-7-Amino-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

Product 1

HCID 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 acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(6R,7R)-7-Amino-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 (1.02 g) (2 mmol) are suspended in 25 ml of water and 25 ml of acetonitrile. While stirring there are added dropwise thereto at 0° C. 27 ml of 0.1N aqueous potassium hydroxide and the solution is treated portionwise with 1.0 g (3 mmol) of 2-amino-4-thiazolethioglyoxylic acid S-(2-benzothiazolyl) ester. The mixture is stirred at 0° C. for 1 hour and at 15°-20° C. for 2 hours. The suspension is now filtered and filter material is washed with water. The mother liquor and wash solution are combined, washed with ethyl acetate and finally acidified (pH~4) with dilute, aqueous hydrochloric acid. The precipitated product is filtered off under suction and washed in succession with water and diethyl ether. After drying in a high vacuum at room temperature there is obtained 0.5 g of (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[(5-(3,4-dihydroxy-phenyl)-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.

Workup

  1. additionare added dropwise
  2. customat 0° C
  3. stirringThe mixture is stirred at 0° C. for 1 hour and at 15°-20° C. for 2 hours
  4. filtrationThe suspension is now filtered
  5. filtrationfilter material
  6. washis washed with water
  7. washThe mother liquor and wash solution
  8. washwashed with ethyl acetate
  9. additionwith dilute
  10. filtrationThe precipitated product is filtered off under suction
  11. washwashed in succession with water and diethyl ether
  12. customAfter drying in a high vacuum at room temperature

Sources & evidence

ORD record
ord-4451f8d02abd48bb839121ce84837c30
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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