Dichloromethane → Tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)propanoate

HRID 453553Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1F)#[N:2].[Cl:19][C:20]1[CH:37]=[CH:36][C:23]([CH2:24][CH2:25][NH:26][C:27](=[O:35])[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:44]CCl>CS(C)=O>[Cl:44][C:22]1[CH:21]=[C:20]([Cl:19])[CH:37]=[CH:36][C:23]=1[CH2:24][CH2:25][NH:26][C:27]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][C:3]=2[C:1]#[N:2])=[CH:30][CH:29]=1)=[O:35]

Participants

Conditions

Temperature: 95 °C

Procedure

A flask was charged with tert-butyl 2-(3-cyano-4-fluorophenyl)propanoate (0.07 g), N-(4-chlorophenethyl)-4-hydroxybenzamide (0.105 g), and potassium carbonate (0.047 g) in 1 ml of DMSO and stirred at 95° C. for one day. The reaction was taken up in dichloromethane and washed with water. The organic layer was collected, dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel chromatography, eluting with a solvent system of 5%-80% ethyl acetate/hexanes gave tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)propanoate (0.102 g).

Workup

washwashed with water
customThe organic layer was collected
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude material was purified by silica gel chromatography
washeluting with a solvent system of 5%-80% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-5b81197b8d634a7cbf4712bfae5cada5
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492437B2

Reaction notes

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