p-Toluenesulfonic acid → HCID 13175153, compound

HRID 2413401Notes

Reaction equation

HRID 2413401 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-Acetamido-thiazol-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 p-toluenesulphonic acid (monohydrate) (2.9 g) dissolved in acetonitrile (20 cc) for 3 hours at 35° C. and 16 hours at 25° C. and then for a further 6 hours at 35° C. after having added further 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 saturated sodium bicarbonate solution (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. Crude 3-(2-acetamido-thiazol-5-yl)-7-amino-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (3.3 g) is obtained 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) and saturated sodium bicarbonate solution (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-ffb843c23f2d4a3ab80bee57069b5ab3
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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