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

HRID 2413448Notes

Reaction equation

HRID 2413448 reaction equation
[CH:1]([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[C:25]1[S:29][C:28]([NH:30][C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[N:34][CH:33]=3)=[N:27][CH:26]=1)[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.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[NH2:39][CH:20]1[C:19](=[O:47])[N:18]2[CH:21]1[S:22][CH2:23][C:24]([C:25]1[S:29][C:28]([NH:30][C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[N:34][CH:33]=3)=[N:27][CH:26]=1)=[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

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 204024552-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-nicotinoylaminothiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 204304287-Amino-2-benzhydryloxycarbonyl-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-eneYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (9 g) in acetonitrile (134 cc) is treated with p-toluenesulphonic acid (7.6 g) according to the working method described in Example 24, to give 7-amino-2-benzhydryloxycarbonyl-3-(2-nicotinoylamino-thiazol-5-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (6.43 g) in the form of a cream powder.

Sources & evidence

ORD record
ord-75f8d224c6e8428588f421f5c0573bc5
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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