Pyridine → HCID 88370434, compound

HRID 263755Notes

Reaction equation

HRID 263755 reaction equation
O[CH2:2]/[CH:3]=[CH:4]/[C@:5]1([CH3:29])[S:11][C@H:10]2[N:7]([C:8](=[O:12])[CH2:9]2)[C@H:6]1[C:13]([O:15][CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14].[F:30][C:31]([F:44])([F:43])[S:32]([O:35]S(C(F)(F)F)(=O)=O)(=[O:34])=[O:33].[N:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C(Cl)Cl>[F:30][C:31]([F:44])([F:43])[S:32]([O-:35])(=[O:34])=[O:33].[CH:16]([O:15][C:13]([C@H:6]1[C@@:5]([CH:4]=[CH:3][CH2:2][N+:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)([CH3:29])[S:11][C@H:10]2[N:7]1[C:8](=[O:12])[CH2:9]2)=[O:14])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 10645194benzhydryl (E)-(2S,3S,5R)-3-(3-hydroxy-propenyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 88370434HCID 88370434, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

410 mg (1.0 mmol) of benzhydryl (E)-(2S,3S,5R)-3-(3-hydroxy- propenyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 6 ml of methylene chloride, cooled to -40° C. and treated with 250 μl (1.5 mmol) of trifluoromethanesulfonic anhydride. After 5 minutes 200 μl (2.50 mmol) of pyridine were added, the mixture was stirred at the same temperature for a further hour and subsequently the cooling bath was removed. The solvent was removed on a rotary evaporator at room temperature, the reaction mixture was taken up in 20 ml of methylene chloride and washed twice with 10 ml of saturated sodium chloride solution each time. Drying over magnesium sulfate, filtration and concentration on a rotary evaporator were carried out. The residual red resin was oxidized without further purification. Yield: 600 mg (97%) of red resin MS: (M+) 471.6 IR (KBr): 1777, 1743, 1630, 1160, 987 cm-1

Workup

  1. customsubsequently the cooling bath was removed
  2. customThe solvent was removed on a rotary evaporator at room temperature
  3. washwashed twice with 10 ml of saturated sodium chloride solution each time
  4. dry with materialDrying over magnesium sulfate, filtration and concentration on a rotary evaporator
  5. customThe residual red resin was oxidized without further purification

Sources & evidence

ORD record
ord-86958c58684a46f4b1bf6bea359f393d
Source dataset
uspto-grants-1997_07
Patent number
US05644053

Reaction notes

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