Acetonitrile → (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 1755861Notes

Reaction equation

HRID 1755861 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]=[CH:18][N:17]=1)=[C:7]2[C:11]([OH:13])=[O:12].[OH-:30].[K+].[C:32](#[N:34])[CH3:33]>O>[NH2:8][C:3]1[S:4][CH:33]=[C:32]([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]=[CH:18][N:17]=2)=[C:7]3[C:11]([OH:13])=[O:12])=[O:30])[N:34]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 14797Potassium Hydroxide2×HCID 54106762(6R,7R)-7-Amino-3-[[[5-(3,4-dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 86748847(6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)-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)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (215 mg) (0.5 mmol) are suspended in 10 ml of water and 5 ml of acetonitrile. At 0° C. there are added dropwise thereto while stirring 7.5 ml of 0.1N aqueous potassium hydroxide solution and after 30 minutes there are added portionwise thereto within one hour 210 mg (0.65 mmol) of 2-amino-4-thiazoleglyoxylic acid S-(2-benzothiazolyl) ester. After a further 5 hours 0.1N aqueous potassium hydroxide solution is added thereto until pH 7.8 has been reached. The suspension obtained is filtered, the filtrate is washed with ethyl acetate and acidified (pH 5) with dilute aqueous hydrochloric acid. The precipitated product is filtered off under suction and washed with water and diethyl ether. After drying in a high vacuum there are obtained 200 mg of (6R,7R)-7-(2-amino-4-thiazoleglyoxylamido)-3-[[[5-(3,4-dihydroxyphenyl)-4-pyrimidinyl]thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a beige powder.

Workup

  1. additionAt 0° C. there are added dropwise
  2. additionafter 30 minutes there are added portionwise
  3. customThe suspension obtained
  4. filtrationis filtered
  5. washthe filtrate is washed with ethyl acetate
  6. filtrationThe precipitated product is filtered off under suction
  7. washwashed with water and diethyl ether
  8. customAfter drying in a high vacuum

Sources & evidence

ORD record
ord-f8757820b83449c2984f90725232c31c
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

Loading…