Pyridine → HCID 68579449, compound

HRID 643988Notes

Reaction equation

HRID 643988 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>C(Cl)Cl>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=1[NH:1][S:27]([C:24]1[CH:23]=[CH:22][C:21]([O:20][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:26][CH:25]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 80001Methyl 4-chloroanthranilateHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chloride

Product 1

HCID 68579449HCID 68579449, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-amino-4-chlorobenzoate (2.5 g, 13.3 mmol) is added to a solution of 2.5 g (8.84 mmol) of the title B compound, 4-benzyloxybenzenesulfonyl chloride in 50 mL of DCM, then 1.4 g (1.43 mL, 17.68 mmol) of pyridine is added. The mixture is stirred overnight at RT. The organic solution is then washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum to a slightly red solid. The solid is adsorbed on 13 g of silica gel and chromatographed (FlashElute 40M silica gel column) using 1 L of an EtOAc (15%)-hexane (85%) mixture as the eluent, followed by 1 L of DCM to afford 2-(4-benzyloxybenzene-sulfonylamino)-4-chloro-benzoic acid methyl ester as a white solid.

Workup

  1. washThe organic solution is then washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum to a slightly red solid
  5. customchromatographed (FlashElute 40M silica gel column)

Sources & evidence

ORD record
ord-769ad796a5e14945852bbd872f10dac6
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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