HCID 131716959, compound → HCID 15629285, compound

HRID 1614347Notes

Reaction equation

HRID 1614347 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 2×500 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 2×500 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-2c3b16a568954e5d9d96113487f8a6e8
Source dataset
uspto-grants-1993_03
Patent number
US05196548

Reaction notes

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