Bis(2-bromoethyl) ether → HCID 178518177、化合物

HRID 46122

反応式

HRID 46122 の反応式
[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

参加物

5

反応物 3

HCID 21521Bis(2-bromoethyl) etherHCID 2724682Lithium diisopropylamideHCID 178516948HCID 178516948、化合物

生成物 1

HCID 178518177HCID 178518177、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-d9390a08a4fb4fd890ff708357bfb600
出典データセット
uspto-grants-2013_09
特許番号
US08541592B2

関連ノート

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