Diisopropylethylamine → HCID 57706543, compound

HRID 1662571

Reaction equation

HRID 1662571 reaction equation
[C:1]([N:4]1[C@H:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][O:6][C:5]1=[O:16])(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[N+:26](/[CH:29]=[CH:30]/[C:31]1[CH:32]=[C:33]([CH:42]=[CH:43][CH:44]=1)[O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([O-:28])=[O:27]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N+:26]([CH2:29][C@@H:30]([C:31]1[CH:44]=[CH:43][CH:42]=[C:33]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:32]=1)[CH2:2][C:1]([N:4]1[C@H:8]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:7][O:6][C:5]1=[O:16])=[O:3])([O-:28])=[O:27]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 735930(R)-3-Acetyl-4-benzyloxazolidin-2-oneHCID 53682823-Benzyloxy-trans-beta-nitrostyrene

Product 1

HCID 57706543HCID 57706543, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalyst2×HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

At −78° C., titanium(iv) chloride (1.0 M solution in DCM) (17.8 mL, 17.8 mmol) was added slowly to a solution of (R)-3-acetyl-4-benzyloxazolidin-2-one (available from Aldrich) (3.55 g, 16.2 mmol) in DCM (80 mL), followed by slow addition of diisopropylethyl amine (3.38 mL, 19.4 mmol). The mixture was stirred at −78° C. for 30 minutes and then a solution of (E)-1-((3-(2-nitrovinyl)phenoxy)methyl)benzene (94.1A) (4.13 g, 16.2 mmol) (commercially available from Aldrich) in DCM (17 mL) was added dropwise (over 15 minutes). Then TiCl4 (16 mL, 1.0 M solution in DCM) was added slowly to the reaction. The mixture was stirred at −78° C. for 2 hours and then quenched with NH4Cl solution. The mixture was extracted with EtOAc (350 mL) and the organic phase was washed with sodium bicarbonate solution and brine, dried over anhydrous Na2SO4. After removing solvent, the residue was recrystallized from MeOH, 94.1B (727 mg), white solid was obtained. MS ESI (np0s.) m/e: 475 (M+H)+.

Workup

  1. stirringThe mixture was stirred at −78° C. for 2 hours
  2. customquenched with NH4Cl solution
  3. extractionThe mixture was extracted with EtOAc (350 mL)
  4. washthe organic phase was washed with sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter removing solvent
  7. customthe residue was recrystallized from MeOH, 94.1B (727 mg)
  8. customwhite solid was obtained

Sources & evidence

ORD record
ord-9aa5c69a1e0f45259d32a0a18720e900
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Linked notes

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