Acetic acid, 2,2-dimethoxy-, methyl ester → N-(5-chloro-2,4-difluorobenzyl)-2,2-dimethoxyacetamide

HRID 1926269Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4](OC)=[O:5].[Cl:10][C:11]1[C:12]([F:20])=[CH:13][C:14]([F:19])=[C:15]([CH:18]=1)[CH2:16][NH2:17]>CCOC(C)=O>[Cl:10][C:11]1[C:12]([F:20])=[CH:13][C:14]([F:19])=[C:15]([CH:18]=1)[CH2:16][NH:17][C:4](=[O:5])[CH:3]([O:8][CH3:9])[O:2][CH3:1]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl dimethoxyacetate (1.45 g, 10.7 mmol) and 5-chloro-2,4-difluorobenzylamine (1.78 g, 10.0 mmol) in a sealed tube was heated at 80° C. for 20 h. After that time, the mixture was diluted with EtOAc (20 ml), washed with HCl (2 N, 10 ml), saturated Na2CO3 (10 ml), H2O (10 ml) and brine (10 ml), and dried over MgSO4. After concentrated in vacuo, the title compound was obtained as a brown oil. 1H NMR (400 MHz, CDCl3): δ=3.41 (s, 6H), 4.46 (d, J=6.4 Hz, 2H), 4.74 (s, 1H), 6.92 (t, J=8.8 Hz, 1H), 6.93 (brs, 1H), 7.41 (t, J=8.0 Hz, 1H). MS(ES+): m/z=280.03/282.01 (95/57) [MH+]. HPLC: tR=3.02 min (polar—5 min, ZQ3).

Workup

washwashed with HCl (2 N, 10 ml), saturated Na2CO3 (10 ml), H2O (10 ml) and brine (10 ml)
dry with materialdried over MgSO4
concentrationAfter concentrated in vacuo

Sources & evidence

ORD record: ord-313e47e72ac24363b3127ef20a684b35
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178668B2

Reaction notes

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