p-Toluenesulfonic acid monohydrate → 7-Amino-2-benzhydryloxycarbonyl-3-(2-mesyloxyprop-1-en-1-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 463585Notes

Reaction equation

HRID 463585 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[CH:25]=[C:26]([O:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH3:27])[CH:20]([NH:33]C(OC(C)(C)C)=O)[C:19]2=[O:41])=[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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C.C(Cl)Cl>[NH2:33][CH:20]1[C:19](=[O:41])[N:18]2[CH:21]1[S:22][CH2:23][C:24]([CH:25]=[C:26]([O:28][S:29]([CH3:32])(=[O:31])=[O:30])[CH3:27])=[C:17]2[C:15]([O:14][CH:1]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:16]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 540532232-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-mesyloxy-prop-1-en-1-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 537460857-Amino-2-benzhydryloxycarbonyl-3-(2-mesyloxyprop-1-en-1-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A solution of the Z form of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3- (2-mesyloxyprop-1-en-1-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (1 g) in acetonitrile (12 cc) is heated to 38° C. A solution of p-toluenesulphonic acid monohydrate (0.63 g) in acetonitrile (10 cc) is added in the course of 20 minutes and the mixture is then kept at 38° C. for 1 hour. It is diluted with methylene chloride (30 cc) and the solution obtained is washed with a saturated solution of sodium bicarbonate (20 cc) and then with distilled water (50 cc), dried over sodium sulphate and concentrated to a volume of 15 cc under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C. This yields a solution of the Z form of 7-amino-2-benzhydryloxycarbonyl-3-(2-mesyloxyprop-1-en-1-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene, to which triethylamine (0.7 cc) is added (Solution A).

Workup

  1. customthe solution obtained
  2. washis washed with a saturated solution of sodium bicarbonate (20 cc)
  3. dry with materialwith distilled water (50 cc), dried over sodium sulphate
  4. concentrationconcentrated to a volume of 15 cc under reduced pressure (20 mm Hg; 2.7 kPa) at 20° C

Sources & evidence

ORD record
ord-935c8b6bc43a4a91a9cc8cfd18a1b52e
Source dataset
uspto-grants-1985_05
Patent number
US04520193

Reaction notes

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