Sodium Chloride → benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3yl)-2-carboxymethoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate

HRID 2351136Notes

Reaction equation

HRID 2351136 reaction equation
[NH2:1][CH:2]1[C:34](=[O:35])[N:4]2[C:5]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:6]([S:9]/[CH:10]=[CH:11]\[C:12]3[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=3)[CH2:7][S:8][C@H:3]12.C[Si](NC(N[Si](C)(C)C)=O)(C)C.CS([O:52][C:53](=O)[C:54]([C:61]1[N:65]=[C:64]([NH2:66])[S:63][N:62]=1)=[N:55][O:56][CH2:57][C:58]([OH:60])=[O:59])(=O)=O.[Cl-].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH2:66][C:64]1[S:63][N:62]=[C:61]([C:54](=[N:55][O:56][CH2:57][C:58]([OH:60])=[O:59])[C:53]([NH:1][CH:2]2[C:34](=[O:35])[N:4]3[C:5]([C:18]([O:20][CH:21]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[O:19])=[C:6]([S:9]/[CH:10]=[CH:11]\[C:12]4[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=4)[CH2:7][S:8][C@H:3]23)=[O:52])[N:65]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 875621,3-Bis(trimethylsilyl)ureaHCID 536554152-(5-Amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetic methanesulfonic anhydrideHCID 67948113benzhydryl 7-amino-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate

Product 1

HCID 131716150benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3yl)-2-carboxymethoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylateYield 59.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of benzhydryl 7-amino-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate (3 g) and bis(trimethylsilyl)urea (3.70 g) in tetrahydrofuran (45 ml) was added 2-(5-amino-1,2,4-thiadiazol-3yl)-2-carboxymethoxyiminoacetic methanesulfonic anhydride (syn isomer) (1.45 g) at -30° C. The mixture was stirred at -20~-10° C. for 1 hour, at 0° C. overnight and at ambient temperature for 2 days. The mixture was poured into a mixture of ethyl acetate and a saturated aqueous solution of sodium chloride. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to give a precipitate. The precipitate was collected and washed with ethyl acetate and diisopropyl ether in turn to give benzhydryl 7-[2-(5-amino-1,2,4-thiadiazol-3yl)-2-carboxymethoxyiminoacetamido]-3-[(Z)-2-(3-pyridyl)vinylthio]-3-cephem-4-carboxylate (syn isomer) (1.95 g).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a precipitate
  5. customThe precipitate was collected
  6. washwashed with ethyl acetate and diisopropyl ether in turn

Sources & evidence

ORD record
ord-dfc4493bb7984891b726e686139fdb82
Source dataset
uspto-grants-1989_10
Patent number
US04871730

Reaction notes

Loading…