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

HRID 2413445Notes

Reaction equation

HRID 2413445 reaction equation
CS(O)(=O)=O.[CH:6]([O:19][C:20]([C:22]1[N:23]2[CH:26]([S:27][CH2:28][C:29]=1[C:30]1[S:34][C:33]([NH:35][C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[N:32][CH:31]=1)[CH:25]([NH:42]C(OC(C)(C)C)=O)[C:24]2=[O:50])=[O:21])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>C(#N)C>[NH2:42][CH:25]1[C:24](=[O:50])[N:23]2[CH:26]1[S:27][CH2:28][C:29]([C:30]1[S:34][C:33]([NH:35][C:36]3[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=3)=[N:32][CH:31]=1)=[C:22]2[C:20]([O:19][CH:6]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:21]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 204024442-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-[2-(pyrid-3-yl-amino)-thiazol-5-yl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene

Product 1

HCID 139605317-Amino-2-benzhydryloxycarbonyl-3-[2-(pyrid-3-yl-amino)-thiazol-5-yl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-eneYield 88.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methanesulphonic acid (37.7 cc) is added, in 5 minutes, to a solution of 2-benzhydryloxycarbonyl-7-t-butoxycarbonylamino-3-[2-(pyrid-3-yl-amino)-thiazol-5-yl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (37.22 g) in acetonitrile (372 cc). The mixture is stirred for 5 minutes and the reaction solution is then added to a mixture of saturated sodium bicarbonate solution (870 cc), distilled water (1740 cc) and methylene chloride (580 cc). The batch is stirred for 10 minutes and the precipitate is filtered off and washed with distilled water (4×100 cc). The product is dried and 7-amino-2-benzhydryloxycarbonyl-3-[2-(pyrid-3-yl-amino)-thiazol-5-yl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (27.66 g) is obtained in the form of a pale yellow crystalline powder.

Workup

  1. distillationdistilled water (1740 cc) and methylene chloride (580 cc)
  2. stirringThe batch is stirred for 10 minutes
  3. filtrationthe precipitate is filtered off
  4. washwashed with distilled water (4×100 cc)
  5. customThe product is dried

Sources & evidence

ORD record
ord-df7d82e6f58748efb64754a759458266
Source dataset
uspto-grants-1985_01
Patent number
US04496560

Reaction notes

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