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Diisopropylethylamine → Benzyl-1,6-diaza-spiro[3.3]heptane-6-carboxylic acid (3-phenyl-propyl)-amide

HRID 2407538
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HRID 2407538 반응식
[CH2:1]([N:8]1[C:11]2([CH2:14][NH:13][CH2:12]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[N:24]([CH2:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[C:25]=[O:26]>ClCCl>[C:30]1([CH2:29][CH2:28][CH2:27][NH:24][C:25]([N:13]2[CH2:12][C:11]3([N:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:9][CH2:10]3)[CH2:14]2)=[O:26])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
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참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 34276663-Phenylpropyl isocyanateHCID 569621441-Benzyl-1,6-diazaspiro[3.3]heptane

생성물 1

HCID 71554979Benzyl-1,6-diaza-spiro[3.3]heptane-6-carboxylic acid (3-phenyl-propyl)-amide수율 12%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-benzyl-1,6-diaza-spiro[3.3]heptane (41 mg, 217 μmol) in dichloromethane (2 mL) was added diisopropyl-ethyl-amine (112 mg, 868 μmol)) followed by (3-isocyanato-propyl)-benzene (84 mg, 521 μmol) and the reaction mixture was allowed to stir at ambient temperature for 16 h. After complete consumption of starting material the reaction mixture was diluted with dichloromethane and was washed successively with water and brine. The organic layer was dried over sodium sulfate and evaporated under reduced pressure. Purification by HPLC afforded the title compound (9 mg, 12%) as an off-white solid. MS m/e: 350 (M+H)+.

후처리

  1. customAfter complete consumption of starting material the reaction mixture
  2. additionwas diluted with dichloromethane
  3. washwas washed successively with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customPurification by HPLC

출처 및 근거

ORD 기록
ord-af2afb0f070048df92e6f5e3aa7c3b69
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08809552B2

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