Diisopropylethylamine → 2-(3,5-Dichloro-2-hydroxy-benzenesulfonylamino)-indan-2-carboxylic acid ethyl ester

HRID 1047687Notes

Reaction equation

HRID 1047687 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([NH2:15])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2].[Cl:16][C:17]1[C:18]([OH:28])=[C:19]([S:24](Cl)(=[O:26])=[O:25])[CH:20]=[C:21]([Cl:23])[CH:22]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([NH:15][S:24]([C:19]2[CH:20]=[C:21]([Cl:23])[CH:22]=[C:17]([Cl:16])[C:18]=2[OH:28])(=[O:25])=[O:26])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chlorideHCID 10921653Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 593143742-(3,5-Dichloro-2-hydroxy-benzenesulfonylamino)-indan-2-carboxylic acid ethyl esterYield 27.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-amino-indan-2-carboxylic acid ethyl ester (3.14 g, 15.3 mmol) and 3,5-dichloro-2-hydroxy-benzenesulfonyl chloride (1 g, 3.82 mmol) in anhydrous DCM (dichloromethane, 20 mL) is added DIPEA (631 μL, 3.82 mmol). The resulting solution is stirred at RT for 1 hour. The reaction solution is diluted in DCM (50 mL) and washed with water (1×5 mL) and brine (2×5 mL). The organic layer is dried over anhydrous Na2SO4 and concentrated in vacuo. The residue is purified by HPLC to give a pure product (30) as white solid (450 mg, 27%).

Workup

  1. washwashed with water (1×5 mL) and brine (2×5 mL)
  2. dry with materialThe organic layer is dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-37032ea8bf1e4e87837147a89bf4d339
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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