Bis(2-bromoethyl) ether → HCID 178518177, compound

HRID 46122

Reaction equation

HRID 46122 reaction equation
[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][CH2:11][C:12](=[O:14])[N:13]=1.[Li+].CC([N-]C(C)C)C.Br[CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br>C1COCC1>[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]2([CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:12](=[O:14])[N:13]=1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 2724682Lithium diisopropylamideHCID 178516948HCID 178516948, compound

Product 1

HCID 178518177HCID 178518177, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To the mixture of 2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)thiazol-4(5H)-one (840 mg, 4.0 mmol) in THF (5.0 mL) was added LDA (2.0 M, 20 mL) at −78° C. The resulting mixture was stirred for 10 min at −78° C., and then 1-bromo-2-(2-bromoethoxy)ethane (3.71 g, 16 mmol) was added. The mixture was allowed to warm to room temperature and then stirred overnight. A sat'd solution of NaH2PO4 was added, and it was extracted with EtOAc. The organic layer was washed with sat'd NH4Cl, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified through flash chromatography (4:1:0.05; CH2Cl2/EtOAc/MeOH) to give the title compound as off-white solid. MS (ES+): 281 (M+H)+.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. extractionit was extracted with EtOAc
  4. washThe organic layer was washed with sat'd NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified through flash chromatography (4:1:0.05; CH2Cl2/EtOAc/MeOH)

Sources & evidence

ORD record
ord-d9390a08a4fb4fd890ff708357bfb600
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Linked notes

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