1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 8-Boc-3,8-diaza-bicyclo(3.2.1)octane

HRID 336132

반응식

HRID 336132 반응식
N1C2C(=CC=CC=2S(NC2C=CC([C:19]([OH:21])=[O:20])=CC=2)(=O)=O)C=CC=1.CCN=C=N[CH2:29][CH2:30][CH2:31]N(C)C.[CH:35]1[CH:36]=[CH:37][C:38]2[N:43](O)N=[N:41][C:39]=2[CH:40]=1.[CH3:45]CN(C(C)C)C(C)C>CN(C=O)C.O>[CH:36]12[N:41]([C:19]([O:21][C:30]([CH3:31])([CH3:45])[CH3:29])=[O:20])[CH:39]([CH2:40][CH2:35]1)[CH2:38][NH:43][CH2:37]2

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 7766454-(Quinoline-8-sulfonamido)benzoic acid

생성물 1

HCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octane

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of acid VIII (0.00021 mol, 1 eq) in DMF (5 mL), EDCI (0.048 g, 0.00024 mol, 1.1 eq), HOBt (0.038 g, 0.00024 mol, 1.1 eq) and DIPEA (0.15 mL, 0.00078 mol, 2.5 eq) were added at 0° C. and stirred for 15 minutes. A solution of amine LXXI (0.00021 mol, 1 eq) was then added at 0° C. and then the resulting mixture was allowed to stir at room temperature for overnight. After completion of the reaction, water (20 mL) was added and extracted with ethyl acetate (2×30 mL). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 60-120 mess, 70% ethyl acetate in hexane) to give compound in 49-55% yield.

후처리

  1. stirringto stir at room temperature for overnight
  2. additionwas added
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography (silica gel, 60-120 mess, 70% ethyl acetate in hexane)
  7. customto give compound in 49-55% yield

출처 및 근거

ORD 기록
ord-381f939f374b4261937448f12cd7e969
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889667B2

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