Nitrogen → HCID 67128447, compound

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), hexamethylenetetramine (1.10 g, 7.79 mmol) and DBU (1.17 mL, 7.75 mmol) were added to a stirred suspension of copper (II) bromide (1.73 g, 7.75 mmol) in deoxygenated dry CH2Cl2 (15 mL). After 20 min, a deoxygenated solution of 2-[3-(2-methyl-[1,3]dioxolan-2-yl)-benzyl]-4,5-dihydro-oxazole-4-carboxylic acid methyl ester (951 mg, 3.12 mmol) in CH2Cl2 (15.0 mL) was added and the reaction mixture was stirred at rt for 45 min. The solvent was removed under reduced pressure and the residue was partitioned between EA (50 mL), and 50 mL of a 1:1 mixture of sat. aq. NH4Cl and 25% aq. NH4OH. The aq. layer was extracted with EA (50 mL) and the combined organic layers were washed with 50 mL of a 1:1 mixture of sat. aq. NH4Cl and 25% aq. NH4OH followed by 10% citric acid (50 mL), sat. aq. NaHCO3 (50 mL) and brine (50 mL). The organic phase was dried over MgSO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (1:1 hept-EA) gave the title compound as a pale yellow solid. TLC: rf (1:1 hept-EA)=0.37. LC-MS-conditions 02: tR=0.93 min, [M+H]+=304.34.

1. customin deoxygenated dry CH2Cl2 (15 mL)
2. customThe solvent was removed under reduced pressure
3. customthe residue was partitioned between EA (50 mL), and 50 mL of a 1:1 mixture of sat. aq. NH4Cl and 25% aq. NH4OH
4. extractionThe aq. layer was extracted with EA (50 mL)
5. washthe combined organic layers were washed with 50 mL of a 1:1 mixture of sat. aq. NH4Cl and 25% aq. NH4OH
6. dry with materialThe organic phase was dried over MgSO4
7. filtrationfiltered
8. customthe solvent was removed under reduced pressure
9. customPurification of the residue by FC (1:1 hept-EA)

ORD record

ord-a9e6de23dc54427d904ec7d63b6c3f97

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674111B2