Triethylamine → HCID 59479413, compound

HRID 1515542Notes

Reaction equation

HRID 1515542 reaction equation
[CH:1]1([S:4][C:5]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:6]=2/[CH:7]=[N:8]/[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:3][CH2:2]1.CCN(CC)CC>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH:1]1([S:4][C:5]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:6]=2[CH:7]2[CH:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:10][CH2:9][NH:8]2)[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 178471610HCID 178471610, compound

Product 1

HCID 59479413HCID 59479413, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 76B (ca 31 mmol) in CH2Cl2 (150 mL) at −15° C. was added Et3N (5.94 mL, 43 mmol) followed by TiCl4 (1.0 M in CH2Cl2, 37.2 mL, 37.2 mmol). The mixture was stirred from −15° C. to rt over 3.0 h before it was quenched with sat. K2CO3 (200 mL) at 0° C. and stirred at rt for 1.0 h. CH2Cl2 was removed under vacuo and EtOAc was added to the crude (for better filtration). The mixture was filtered through a pad of wet Celite®, extracted with EtOAc (3×100 mL). The organic layer was washed with water, dried over Na2SO4. The cude was purified by silica gel flash column chromatography using gradient CH2Cl2 in hexanes to give 76C (3.77 g, 56% yield) and retrieved 76A (2.8 g). LC-MS indicated a mixture of cis and trans isomer in ca. 1:1 ratio. LC-MS 337 (M+H).

Workup

  1. customwas quenched with sat. K2CO3 (200 mL) at 0° C.
  2. stirringstirred at rt for 1.0 h
  3. customCH2Cl2 was removed under vacuo and EtOAc
  4. additionwas added to the crude (for better filtration)
  5. filtrationThe mixture was filtered through a pad of wet Celite®
  6. extractionextracted with EtOAc (3×100 mL)
  7. washThe organic layer was washed with water
  8. dry with materialdried over Na2SO4
  9. customThe cude was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-d533cc28e9304e53b1d81b126963a4d9
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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