Pyridine → HCID 69356473, compound

HRID 852550Notes

Reaction equation

HRID 852550 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:20])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]=[C:7]([NH2:19])[CH:6]=1.N1C=CC=CC=1.[Cl:27][CH2:28][CH2:29][CH2:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:2][O:3][C:4](=[O:20])[C:5]1[CH:6]=[C:7]([NH:19][S:31]([CH2:30][CH2:29][CH2:28][Cl:27])(=[O:33])=[O:32])[CH:8]=[C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:10]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 154103-Chloropropanesulphonyl chlorideHCID 69358979706792-05-4

Product 1

HCID 69356473HCID 69356473, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A suspension of 3-amino-5-benzyloxy-benzoic acid methyl ester hydrochloride (D50) (5.0 g, 17 mmol, 1 equiv) in CH2Cl2 (100 ml) was treated with DMAP (400 mg, 3.2 mmol) and pyridine (3.5 g, 44 mmol, 2.6 equiv) followed by 3-chloropropanesulfonyl chloride (3.54 g, 20 mmol, 1.2 equiv) dropwise at room temperature. The resulting mixture was stirred for 16 h then concentrated in vacuo. The residue was dissolved in AcOEt (200 ml) and the resulting solution was washed with 2N aqueous HCl solution (100 ml) followed by saturated aqueous NaHCO3 solution (100 ml), dried over MgSO4 and concentrated in vacuo to give 3-benzyloxy-5-(3-chloro-propane-1-sulfonylamino)-benzoic acid methyl ester (D52) (6.0 g, 97%) as a pale pink solid. [M+H]+=366.1, RT=2.34 min

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in AcOEt (200 ml)
  3. washthe resulting solution was washed with 2N aqueous HCl solution (100 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1df2f2cf93a241c5b75f626398f5fe34
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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