Dimethyl Sulfoxide → HCID 57277696, compound

HRID 726990Notes

Reaction equation

HRID 726990 reaction equation
CS(C)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:43]=[CH:44][C:45]=1[O:46][CH3:47])[CH2:23][N:24]1[C:30](=[O:31])[C@@H:29]2[C@H:25]1[C@@H:26]([OH:42])[CH2:27][N:28]2[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:43]=[CH:44][C:45]=1[O:46][CH3:47])[CH2:23][N:24]1[C:30](=[O:31])[C@@H:29]2[C@H:25]1[C:26](=[O:42])[CH2:27][N:28]2[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 9845Trifluoroacetic anhydrideHCID 81531DiisopropylethylamineHCID 10787818HCID 10787818, compound

Product 1

HCID 57277696HCID 57277696, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

3.7 g (47 mmol) of DMSO were dissolved in 50 ml of methylene chloride and cooled to -78° C. under argon. Then, 5 ml (35 mmol) of trifluoroacetic acid anhydride were added dropwise thereto, the mixture was stirred for 15 minutes and a solution of 9.7 g (23.5 mmol) of benzyl (1S,4S,5S)-6(3,4-dimethoxybenzyl)-4-hydroxy-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate in 50 ml of methylene chloride was slowly added dropwise thereto and left to react for 1.5 hours. Before it was left to warm to room temperature, 12 ml (70 mmol) of ethyldiisopropylamine were added thereto. The reaction mixture was then washed once each time with dilute aqueous hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution and the organic phase was dried over magnesium sulphate. After concentration there were obtained 9.5 g (98%) of a yellow oil.

Workup

  1. waitleft
  2. customto react for 1.5 hours
  3. waitBefore it was left
  4. temperatureto warm to room temperature
  5. washThe reaction mixture was then washed once each time with dilute aqueous hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride solution
  6. dry with materialthe organic phase was dried over magnesium sulphate
  7. concentrationAfter concentration

Sources & evidence

ORD record
ord-70c1c8959adc4a0cb6175147fabe1ab4
Source dataset
uspto-grants-1998_01
Patent number
US05712268

Reaction notes

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