Hydrochloric Acid → HCID 86698881, compound

HRID 527239Notes

Reaction equation

HRID 527239 reaction equation
N#N.[Si:3]([O:10][CH2:11][C:12]1[O:13][CH:14]=[C:15]([C:17]([O-:19])=O)[N:16]=1)([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:5])[CH3:4].[CH2:20]([Mg]Br)[CH3:21].Cl>C1COCC1.CCOCC.C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C.CC(=O)OCC>[Si:3]([O:10][CH2:11][C:12]1[O:13][CH:14]=[C:15]([C:17]2([OH:19])[CH2:21][CH2:20]2)[N:16]=1)([C:6]([CH3:7])([CH3:8])[CH3:9])([CH3:4])[CH3:5]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 86698882HCID 86698882, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 86698881HCID 86698881, compound

Reagents, catalysts & solvents 4

HCID 178460666HCID 178460666, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of method 2-(((tert-butyldimethylsilyl)oxy)methyl)oxazole-4-carboxylate (3.00 g, 11.05 mmol) in THF (110 mL) was treated with tetraisopropoxytitanium (IV) (3.27 mL, 11.05 mmol). To the resulting solution at rt, was added, over 30 min, via syringe pump, ethyl magnesium bromide (18.4 mL of a 3M sol. in ether, 55.27 mmol) and the resulting solution was stirred at rt for 3 h. EA (100 mL) and 1N HCl (50 mL) were added. The layers were separated and the aq. layer was extracted with EA (2×100 mL) and the combined org. layers were washed with sat. aq. sodium bicarbonate (200 mL), brine (200 mL). The org. layer was dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a yellow oil: TLC: rf (4:1 hept-EA)=0.28. LC-MS-conditions 06: tR=0.92 min, [M+H]+=270.41.

Workup

  1. customThe layers were separated
  2. extractionthe aq. layer was extracted with EA (2×100 mL)
  3. washlayers were washed with sat. aq. sodium bicarbonate (200 mL), brine (200 mL)
  4. dry with materiallayer was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure
  7. customPurification of the residue by FC (4:1 hept-EA)

Sources & evidence

ORD record
ord-4b279eaab77f476087d4a2971836f6a6
Source dataset
uspto-grants-2016_05
Patent number
US09346793B2

Reaction notes

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