Sodium Hydroxide → benzhydryl (6R,7R)-7-[[(2Z)-2-acetyloxyimino-2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-3-(pyridin-4-ylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 992696Notes

Reaction equation

HRID 992696 reaction equation
[NH2:1][C@@H:2]1[C:33](=[O:34])[N:4]2[C:5]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:6]([S:9][CH2:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[CH2:7][S:8][C@H:3]12.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.Cl.[NH2:48][C:49]1[S:50][CH:51]=[C:52](/[C:54](=[N:58]/[O:59][C:60](=[O:62])[CH3:61])/[C:55](Cl)=[O:56])[N:53]=1.[OH-].[Na+]>ClCCl.CO.O>[NH2:48][C:49]1[S:50][CH:51]=[C:52](/[C:54](=[N:58]/[O:59][C:60](=[O:62])[CH3:61])/[C:55]([NH:1][C@@H:2]2[C:33](=[O:34])[N:4]3[C:5]([C:17]([O:19][CH:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[O:18])=[C:6]([S:9][CH2:10][C:11]4[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=4)[CH2:7][S:8][C@H:3]23)=[O:56])[N:53]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 11708267BistrimethylsilylacetamidHCID 14770493[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-chloro-2-oxoethylidene]amino] acetate;hydrochlorideHCID 70124524Diphenylmethyl 7beta-amino-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate

Product 1

HCID 88178984benzhydryl (6R,7R)-7-[[(2Z)-2-acetyloxyimino-2-(2-amino-1,3-thiazol-4-yl)acetyl]amino]-8-oxo-3-(pyridin-4-ylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 77%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

Diphenylmethyl 7β-amino-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate (2.15 g, 4.39 m mol) was dissolved in dichloromethane (50 ml) by addition of bis(trimethylsilyl)acetamide (1.79 g, 8.78 m mol). To a resulting solution was added 2-(2-aminothiazol-4-yl)-2-(Z)-(acetoxyimino)acetyl chloride hydrochloride (1.50 g, 5.27 m mol) at 5° C. and the mixture was stirred at 5° C. for 1.5 hours and at room temperature for 16 hours. The mixture was poured into a mixture of water and methanol and adjusted to pH 7 by addition of 1N NaOH aq. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo to give diphenylmethyl 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(acetoxyimino)acetamido]-3-[(4-pyridyl)methylthio]-3-cephem-4-carboxylate (2.37 g).

Workup

  1. customwas separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-53de17a4be0e4238ae22e12174ee5d39
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

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