4-Toluenesulfonyl chloride → HCID 57114913, compound

HRID 1786550Notes

Reaction equation

HRID 1786550 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9]([OH:11])[CH2:8][N:7]1[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:5].[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH3:1][CH2:2][O:3][C:4]([C@@H:6]1[CH2:10][C@@H:9]([O:11][S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[CH2:8][N:7]1[C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])=[O:5]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 12709318HCID 12709318, compound

Product 1

HCID 57114913HCID 57114913, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of (2S,4R)-4-hydroxy-pyrrolidine-1,2-dicarboxylic acid-1-tert-butyl ester-2-ethyl ester (27) (1.8 g, 7 mmol) in dry pyridine (40 ml) was added p-toluenesulfonyl chloride (4.0 g, 21 mmol) under nitrogen at 0° C. The reaction mixture was kept refrigerated at 0° C. for 2 days. The reaction was then concentrated under reduced pressure. The residue was dissolved in ethyl acetate: water (10:1) (150 ml). The organic was washed with water (30 ml, 2×), dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using pet ether: EtOAc (1:1) to give 2.6 g of desired product.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate: water (10:1) (150 ml)
  3. washThe organic was washed with water (30 ml, 2×)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-5dc719d2fa02420b85b134fb57840152
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Reaction notes

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