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N-bromobutanimide → Pyrrolidine-1,2-dicarboxylic acid 2-[2-(5-bromo-3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester

HRID 71995
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인쇄 미리보기

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HRID 71995 반응식
[S:1]1[C:5]([C:6](=[O:23])[CH2:7][O:8][C:9]([CH:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10])=[CH:4][CH:3]2[S:24][CH:25]=[CH:26][CH:2]12.[Br:27]N1C(=O)CCC1=O>CN(C=O)C.CCOC(C)=O>[C:19]([O:18][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][CH:11]1[C:9]([O:8][CH2:7][C:6]([C:5]1[S:1][CH:2]2[CH:26]=[C:25]([Br:27])[S:24][CH:3]2[CH:4]=1)=[O:23])=[O:10])=[O:17])([CH3:20])([CH3:21])[CH3:22]
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참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 66620078Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[2-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester

생성물 1

HCID 66620153Pyrrolidine-1,2-dicarboxylic acid 2-[2-(5-bromo-3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester수율 66%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

실험 절차

Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[2-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester (595 mg, 1.5 mmol) was dissolved in DMF (7.5 mL) and treated with N-bromosuccinimide (295 mg, 1.65 mmol). The reaction mixture was stirred for 4d at RT then diluted with EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (20% to 50% EtOAc/Hex) to afford the title compound (469 mg, 66%).

후처리

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica column chromatography (20% to 50% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-e2904203544f42fbaefaa7a5c5ff1067
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08822430B2

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