tert-Butyl bromoacetate → (S)-tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetate

HRID 2388671노트

반응식

HRID 2388671 반응식
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[C:15]([S:19]([N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][C@H:23]2[CH2:32][OH:33])(=[O:21])=[O:20])=[C:14]([CH3:34])[CH:13]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C1(C)C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH3:34])[C:15]([S:19]([N:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:25][CH2:24][C@H:23]2[CH2:32][O:33][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])(=[O:20])=[O:21])=[C:16]([CH3:18])[CH:17]=1

참가 물질

6

반응물 2

HCID 79177tert-Butyl bromoacetateHCID 57916293(S)-(1-(4-methoxy-2,6-dimethyl-phenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methanol

생성물 1

HCID 57916258(S)-tert-Butyl 2-((1-(4-methoxy-2,6-dimethylphenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methoxy)acetate

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매2회HCID 14798Sodium Hydroxide용매

실험 절차

tert-Butyl 2-bromoacetate (1.358 g, 6.972 mmol) and tetra-n-butylammonium hydrogen sulfate (110 mg, 0.332 mmol) were stirred in sodium hydroxide solution (26 ml, 50% aq) and toluene (20 ml). A solution of (S)-(1-(4-methoxy-2,6-dimethyl-phenylsulfonyl)-1,2,3,4-tetrahydroquinolin-2-yl)methanol (1.2 g, 3.32 mmol) in toluene (10 ml) was added slowly. The addition was exothermic, cooling was achieved with an ice bath. After stirring at room temperature for 1 h, the phases were separated and the aqueous phase was extracted with diethylether (2×50 ml). The combined organic phases were washed with saturated sodium chloride solution (30 ml), dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 5/1.

후처리

  1. additionThe addition
  2. temperaturecooling
  3. customwas achieved with an ice bath
  4. customthe phases were separated
  5. extractionthe aqueous phase was extracted with diethylether (2×50 ml)
  6. washThe combined organic phases were washed with saturated sodium chloride solution (30 ml)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by column chromatography (silica gel) with hexane/ethyl acetate 5/1

출처 및 근거

ORD 기록
ord-a7672e093f01445993888101191ef59a
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268814B2

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