Pyridine → HCID 69356882, compound

HRID 852561Notes

Reaction equation

HRID 852561 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:5]=[C:6]([CH:14]=[C:15]([NH2:17])[CH:16]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].N1C=CC=CC=1.[Cl:25][CH2:26][CH2:27][CH2:28][S:29](Cl)(=[O:31])=[O:30]>CN(C1C=CN=CC=1)C.C(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:5]=[C:6]([CH:14]=[C:15]([NH:17][S:29]([CH2:28][CH2:27][CH2:26][Cl:25])(=[O:31])=[O:30])[CH:16]=1)[C:7]([O:9][C:10]([CH3:13])([CH3:11])[CH3:12])=[O:8]

Participants

7

Reactant 3

HCID 1049PyridineHCID 154103-Chloropropanesulphonyl chlorideHCID 67512486HCID 67512486, compound

Product 1

HCID 69356882HCID 69356882, compoundYield 99.5%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-amino-isophthalic acid 1-tert-butyl ester 3-methyl ester (D79) (5.0 g, 20 mmol, 1 equiv), DMAP (0.3 g, 2.46 mmol, 0.12 equiv) and pyridine (1.64 g, 20 mmol, 1 equiv) in CH2Cl2 (80 ml) was added 3-chloropropanesulfonyl chloride (2.4 ml, 20 mmol, 1 equiv) dropwise. The resulting mixture was stirred for 16 h then diluted with AcOEt (150 ml). The organic phase was washed with 2N aqueous HCl solution and saturated aqueous NaHCO3 solution, dried over MgSO4 and concentrated in vacuo to give 5-(3-chloro-propane-1-sulfonylamino)-isophthalic acid 1-tert-butyl ester 3-methyl ester (D81) (7.8 g, 99%) as a pale orange solid.

Workup

  1. washThe organic phase was washed with 2N aqueous HCl solution and saturated aqueous NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c00cfb4c4deb4bb2b236983ebabc4de1
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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