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

HRID 46122

반응식

HRID 46122 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 178518177HCID 178518177, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-d9390a08a4fb4fd890ff708357bfb600
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541592B2

연결된 노트

불러오는 중…