1,2-Dichloroethane → HCID 11327231, compound

HRID 238924Notes

Reaction equation

HRID 238924 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:13]([CH3:17])[C:14]([OH:16])=O)[CH:5]=[CH:6][C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[C:18]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19].C(Cl)CCl>C(Cl)Cl>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([CH2:26][NH:27][C:14](=[O:16])[CH:13]([C:4]2[CH:5]=[CH:6][C:7]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])=[C:2]([F:1])[CH:3]=2)[CH3:17])=[CH:28][CH:29]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 27356554-tert-ButylbenzylamineHCID 24754387HCID 24754387, compound

Product 1

HCID 11327231HCID 11327231, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture consisting of 2-[3-Fluoro-4-(methylsulfonylamino)phenyl]propionic acid (1-38, 10 mmol), 4-t-butylbenzylamine (12 mmol) and EDC (12 mmol) in CH2Cl2 (20 mL) was stirred for 12 h at room temperature. The reaction mixture was filtered off and the filtrate was concentrated. the residue was purified by flash column chromatography on silica gel using EtOAc:hexanes as eluant to obtain N-(4-tert-butylbenzyl)-2-[3-fluoro-4-(metylsulfonylamino)phenyl]propionamide (1-51, KMJ-372) having following physicochemical properties:

Workup

  1. filtrationThe reaction mixture was filtered off
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-9b9134eaa1d14ab09e3a68420ba0f8fb
Source dataset
uspto-grants-2014_02
Patent number
US08642657B2

Reaction notes

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