2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide → 7-Amino-2-benzhydryloxycarbonyl-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide

HRID 851569Notes

Reaction equation

HRID 851569 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22](=[O:38])[CH2:23][C:24]=1[CH:25]=[CH:26][O:27][S:28]([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29])[CH:20]([NH:39]C(OC(C)(C)C)=O)[C:19]2=[O:47])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C>[NH2:39][CH:20]1[C:19](=[O:47])[N:18]2[CH:21]1[S:22](=[O:38])[CH2:23][C:24]([CH:25]=[CH:26][O:27][S:28]([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29])=[C:17]2[C:15]([O:14][CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:16]

Participants

3

Reactant 1

HCID 543826532-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide

Product 1

HCID 539396637-Amino-2-benzhydryloxycarbonyl-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxideYield 60.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the E form of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (54.3 g) and hydrated p-toluenesulphonic acid (30.4 g) in acetonitrile (1.4 liters) is stirred at 35° C. for 2 hours. The mixture is concentrated to dryness at 30° C. under 20 mm Hg (2.7 kPa), the residue is taken up in ethyl acetate (1 liter) and the mixture is washed with a semi-saturated solution of sodium bicarbonate (2×500 cc) and a semi-saturated solution of sodium chloride (2×500 cc), dried over sodium sulphate and concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa). The residue is triturated in ether (200 cc). This yields the E form of 7-amino-2-benzhydryloxycarbonyl-8-oxo-3-(2-tosyloxyvinyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (28.13 g) in the form of a light brown powder.

Workup

  1. concentrationThe mixture is concentrated to dryness at 30° C. under 20 mm Hg (2.7 kPa)
  2. washthe mixture is washed with a semi-saturated solution of sodium bicarbonate (2×500 cc)
  3. dry with materiala semi-saturated solution of sodium chloride (2×500 cc), dried over sodium sulphate
  4. concentrationconcentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)
  5. customThe residue is triturated in ether (200 cc)

Sources & evidence

ORD record
ord-4daeee5e0c6d493da089d8dd814a46bc
Source dataset
uspto-grants-1983_05
Patent number
US04385181

Reaction notes

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