4-Toluenesulfonyl chloride → HCID 22854930, compound

HRID 1901434Notes

Reaction equation

HRID 1901434 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4]1[CH2:8][C@@H:7](O)[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].C(N(CC)CC)C.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[C@H:4]1[CH2:8][C@@H:7]([S:34]([C:31]2[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=2)(=[O:36])=[O:35])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 6884101-Benzyl 2-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

Product 1

HCID 22854930HCID 22854930, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

A solution of 20 g (71.6 mmol) of N-Cbz-cis-4-hydroxy-D-proline methyl ester, 15 mL (107 mmol) of triethylamine and 0.4 g (3.3 mmol) of 4-dimethylaminopyridine in 200 mL of CHCl3 was treated with 15.1 g (79.2 mmol) of p-toluenesulfonyl chloride in portions. The reaction was stirred at room temperature for 18 hours and was washed successively with 100 mL of H2O, 100 mL of 1N aqueous citric acid, and 100 mL of H2O. The organic fraction was dried over Na2SO4 and evaporated in vacuo to give 31.4 g of an oil which was purified by flash chromatography (SiO2 ; 50 percent EtOAc in hexanes) to afford 18.2 g (42 mmol; 59 percent) of the title compound as a white solid.

Workup

  1. washwas washed successively with 100 mL of H2O, 100 mL of 1N aqueous citric acid, and 100 mL of H2O
  2. dry with materialThe organic fraction was dried over Na2SO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-97a9cfdfa647429186fd8b9d319cf84c
Source dataset
uspto-grants-1996_11
Patent number
US05578574

Reaction notes

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