p-Toluenesulfonic acid → HCID 13175153, compound

HRID 370596Notes

Reaction equation

HRID 370596 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([C:10]2[CH2:17][S:16][CH:15]3[N:12]([C:13](=[O:26])[CH:14]3[NH:18]C(OC(C)(C)C)=O)[C:11]=2[C:27]([O:29][CH:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])=[CH:8][N:9]=1)(=[O:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[C:1]([NH:4][C:5]1[S:6][C:7]([C:10]2[CH2:17][S:16][CH:15]3[N:12]([C:13](=[O:26])[CH:14]3[NH2:18])[C:11]=2[C:27]([O:29][CH:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:28])=[CH:8][N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acid2×HCID 13175939HCID 13175939, compound

Product 1

HCID 13175153HCID 13175153, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

3-(2-Acetamidothiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (4.6 g) is dissolved in acetonitrile (190 cc) at 35° C. and treated with a solution of p-toluenesulphonic acid (monohydrate) (2.9 g) in acetonitrile (20 cc) for 3 hours at 35° C., for 16 hours at 25° C. and then for a further 6 hours at 35° C. after the addition of p-toluenesulphonic acid (monohydrate) (0.95 g). The reaction mixture is partially concentrated under reduced pressure (30 mm Hg; 4 kPa) at 30° C. and then diluted with methylene chloride (200 cc) and a saturated solution of sodium bicarbonate (200 cc). The aqueous layer is extracted with methylene chloride (100 cc) and the combined organic solutions are washed with water (200 cc) and then dried and concentrated under reduced pressure (30 mm Hg; 4 kPa) at 30° C. The residue is dried under reduced pressure (10 mm Hg; 1.3 kPa) at 25° C. This gives crude 3-(2-acetamidothiazol-5-yl)-7-amino-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (3.3 g) in the form of a beige powder.

Workup

  1. concentrationThe reaction mixture is partially concentrated under reduced pressure (30 mm Hg; 4 kPa) at 30° C.
  2. additiondiluted with methylene chloride (200 cc)
  3. extractionThe aqueous layer is extracted with methylene chloride (100 cc)
  4. washthe combined organic solutions are washed with water (200 cc)
  5. customdried
  6. concentrationconcentrated under reduced pressure (30 mm Hg; 4 kPa) at 30° C
  7. customThe residue is dried under reduced pressure (10 mm Hg; 1.3 kPa) at 25° C

Sources & evidence

ORD record
ord-88ecc2b08b1d427caf42c126eef32736
Source dataset
uspto-grants-1985_07
Patent number
US04526962

Reaction notes

Loading…