Acetic acid, 2,2-dimethoxy-, methyl ester → HCID 67520892, compound

HRID 1926284Notes

Reaction equation

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

Participants

Reactant 2

HCID 66647Acetic acid, 2,2-dimethoxy-, methyl ester

HCID 673264-Fluorobenzylamine

Product 1

HCID 67520892HCID 67520892, compound

Conditions

Temperature: 60 °C

Procedure

Into a sealable tube were added methyl dimethoxyacetate (0.98 g, 7.3 mmol) and 4-fluorobenzylamine (0.91 g, 7.3 mmol); mixture was stirred at 60° C. for 2 days. The compound was purified by column chromatography on silica gel (10 g/70 mL prepacked cartridge, eluting with 5% EtOAc in hexanes→5% MeOH in hexanes), affording the title compound. HPLC: tR=2.58 min. (ZQ2, polar—5 min.). MS (ES+): m/z=249.92 (24) [MNa+], 227.91 (100) [MH+].

Workup

customThe compound was purified by column chromatography on silica gel (10 g/70 mL prepacked cartridge, eluting with 5% EtOAc in hexanes→5% MeOH in hexanes)

Sources & evidence

ORD record: ord-56ede2a1ceec426198f5a1179cd13ac1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178668B2

Reaction notes

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