p-Toluenesulfonic acid monohydrate → 3-Acetonyl-7-amino-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 463590Notes

Reaction equation

HRID 463590 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:13]([C:17]1[CH2:24][S:23][CH:22]2[N:19]([C:20](=[O:33])[CH:21]2[NH:25]C(OC(C)(C)C)=O)[C:18]=1[C:34]([O:36][CH:37]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:35])[C:14]([CH3:16])=[O:15]>C(#N)C>[CH2:13]([C:17]1[CH2:24][S:23][CH:22]2[N:19]([C:20](=[O:33])[CH:21]2[NH2:25])[C:18]=1[C:34]([O:36][CH:37]([C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)=[O:35])[C:14]([CH3:16])=[O:15]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 132333103-Acetonyl-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 202811313-Acetonyl-7-amino-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of p-toluenesulphonic acid monohydrate (3.8 g) in acetonitrile (50 cc) is added, in the course of 30 minutes, to a solution of 3-acetonyl-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (5.23 g) in acetonitrile (50 cc) at 40° C. The mixture is kept at 40° C. for 30 minutes and then concentrated under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. to a volume of about 30 cc. It is diluted with methylene chloride (150 cc) and the solution is washed with a saturated aqueous solution of sodium bicarbonate (50 cc) and dried over magnesium sulphate. This yields a solution of 3-acetonyl-7-amino-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene, which is identical to the product described in Reference Example 2.

Workup

  1. concentrationconcentrated under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. to a volume of about 30 cc
  2. additionIt is diluted with methylene chloride (150 cc)
  3. washthe solution is washed with a saturated aqueous solution of sodium bicarbonate (50 cc)
  4. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-5d63fc941c6f4bc4a5e5ef5a19805937
Source dataset
uspto-grants-1985_05
Patent number
US04520193

Reaction notes

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