tert-Butyl bromoacetate → HCID 69103938, 화합물

HRID 1353585노트

반응식

HRID 1353585 반응식
[S:1]1[CH:5]=[C:4]([CH2:6][CH2:7][C:8]([N:10]2[CH:14]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:13][O:12][C:11]2=[O:22])=[O:9])[C:3]2[CH:23]=[CH:24][CH:25]=[CH:26][C:2]1=2.C([N-]C(C)C)(C)C.[Li+].Br[CH2:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38]>O1CCCC1>[C:40]([O:39][C:37](=[O:38])[CH2:36][C@H:7]([CH2:6][C:4]1[C:3]2[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=2[S:1][CH:5]=1)[C:8]([N:10]1[CH:14]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:13][O:12][C:11]1=[O:22])=[O:9])([CH3:43])([CH3:42])[CH3:41]

참가 물질

5

반응물 3

HCID 79177tert-Butyl bromoacetateHCID 2724682Lithium diisopropylamideHCID 21102160HCID 21102160, 화합물

생성물 1

HCID 69103938HCID 69103938, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3-(3-benzo[b]thiophen-3-yl-propionyl)-4-benzyl-oxazolidin-2-one (3.35 g, 9.18 mmol) in 100 mL anhydrous tetrahydrofuran at −78° C. was added lithium diisopropyl amide in tetrahydrofuran (6.1 mL, 11.01 mmol) and the reaction mixture was stirred for 30 min Following addition of t-butyl bromoacetate (1.62 mL, 11.01 mmol) at −78° C., the mixture was stirred overnight while it was allowed to warm to room temperature. The solvent was evaporated and the residue diluted with ethyl acetate. The organic layer was washed with water (3×100 mL), dried, filtered, and concentrated to give the crude product. The title product was obtained by filtration through a pad of silica, eluting with methylene chloride (49%).

후처리

  1. stirringthe mixture was stirred overnight while it
  2. customThe solvent was evaporated
  3. additionthe residue diluted with ethyl acetate
  4. washThe organic layer was washed with water (3×100 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product

출처 및 근거

ORD 기록
ord-4a469470009047ac88859b1142eebaa4
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220862B2

반응 노트

불러오는 중…