HCID 131716959, compound → HCID 15629285, compound

HRID 1087622Notes

Reaction equation

HRID 1087622 reaction equation
C[CH:2]1N(CC2C=CC=CC=2)C(=O)N(C2C=CC(Cl)=CC=2)[C:3]1=[O:4].[CH2:23]([O:25][C:26](=[O:53])[C@H:27]1[CH2:31][CH:30]([O:32]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:29][N:28]1[S:43]([C:46]1[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=1)(=[O:45])=[O:44])[CH3:24]>C1(C)C=CC=CC=1.C([O-])(=O)C.C[N+](C)(C)C>[CH2:23]([O:25][C:26](=[O:53])[C@H:27]1[CH2:31][CH:30]([O:32][C:3](=[O:4])[CH3:2])[CH2:29][N:28]1[S:43]([C:46]1[CH:51]=[CH:50][C:49]([CH3:52])=[CH:48][CH:47]=1)(=[O:44])=[O:45])[CH3:24]

Participants

4

Reactant 1

HCID 131716959HCID 131716959, compound

Product 1

HCID 15629285HCID 15629285, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 82741Tetramethylammonium acetateCatalystHCID 1140TolueneSolvent

Procedure

To 218 g (466 mmol) of allo-1-(4-toluenesulfonyl)- 4-(4-toluenesulfonyloxy)-D-proline ethyl ester in 1500 ml of toluene was added 81 g (606 mmol) of tetramethyl ammonium acetate and the mixture was heated to reflux for 2 hours. The reaction was cooled, washed with 2x500 ml of water and dried over sodium sulfate. Evaporation of the solvent and drying the resulting solids in a vacuum oven overnight at 30° C. provided 120.6 g of product (72% yield). M.P.=82°-83° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction was cooled
  4. washwashed with 2x500 ml of water
  5. dry with materialdried over sodium sulfate
  6. customEvaporation of the solvent
  7. customdrying the resulting solids in a vacuum oven overnight at 30° C.

Sources & evidence

ORD record
ord-58d0e12a7c554d2488f820e440a85761
Source dataset
uspto-grants-1991_07
Patent number
US05036153

Reaction notes

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