Methanesulfonic Acid → 7-Amino-3-(2-benzamido-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

HRID 2413405Notes

Reaction equation

HRID 2413405 reaction equation
[C:1]([NH:9][C:10]1[S:11][C:12]([C:15]2[CH2:22][S:21][CH:20]3[N:17]([C:18](=[O:31])[CH:19]3[NH:23]C(OC(C)(C)C)=O)[C:16]=2[C:32]([O:34][CH:35]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])=[CH:13][N:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(O)(=O)=O>C(#N)C>[NH2:23][CH:19]1[C:18](=[O:31])[N:17]2[CH:20]1[S:21][CH2:22][C:15]([C:12]1[S:11][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:14][CH:13]=1)=[C:16]2[C:32]([O:34][CH:35]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 131759503-(2-Benzamidothiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 131759567-Amino-3-(2-benzamido-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-eneYield 81.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(2-benzamido-thiazol-5-yl)-2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2.9 g) in acetonitrile (29 cc) is treated with methanesulphonic acid (2.9 cc) using the working method of Example 15. Crude 7-amino-3-(2-benzamido-thiazol-5-yl)-2-benzhydryloxycarbonyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2 g) is obtained in the form of a yellow froth.

Sources & evidence

ORD record
ord-7dd784caa00d4b9aa638bee904639569
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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