1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59668673, 화합물

HRID 2191883노트

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HRID 2191883 반응식
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:22][CH2:21][CH2:20][C@@:19]3([CH3:26])[C:23](O)=[O:24])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[NH2:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][C:35]([Br:38])=[CH:34][CH:33]=1)=[O:31].C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.O>[Br:38][C:35]1[CH:36]=[CH:37][C:32]([C:30](=[O:31])[CH2:29][NH:28][C:23]([C@:19]2([CH3:26])[CH2:20][CH2:21][CH2:22][N:18]2[C:16]([O:15][CH2:14][CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[O:17])=[O:24])=[CH:33][CH:34]=1

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27982162-Amino-1-(4-bromophenyl)ethan-1-one hydrochlorideHCID 59772286(2S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-2-methylpyrrolidine-2-carboxylic acid

생성물 1

HCID 59668673HCID 59668673, 화합물수율 102%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To (S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-2-methylpyrrolidine-2-carboxylic acid (intermediate LS30; 1.5 g; 4.3 mmol) in 50 mL DMF was added sequentially 2-amino-1-(4-bromophenyl)ethanone hydrochloride (1.2 g; 4.7 mmol), HOAT (290 mg; 2.1 mmol), Hunig's base (0.7 mL; 4.3 mmol) and EDCI (1.2 g; 6.4 mmol). After 1 h, the reaction mixture was poured into 150 mL water and allowed to stir for 15 min before filtering the resultant precipitate which was dissolved in dichloromethane and dried over magnesium sulfate. The dichloromethane mixture was filtered and applied to a Biotage 40 samplet. Chromatography on a 40M column (25 to 60% ethyl acetate/hexane over 1200 mL) provided (S)-(9H-fluoren-9-yl)methyl 2-(2-(4-bromophenyl)-2-oxoethylcarbamoyl)-2-methylpyrrolidine-1-carboxylate (intermediate LS31; 2.4 g; quant) as a yellow foam. LC (Cond'n 11): RT=3.75 min; MS: Anal. Calcd. for [M+H]+ C29H27BrN2O4: 547.1; found 547.0.

후처리

  1. filtrationbefore filtering the resultant precipitate which
  2. dissolutionwas dissolved in dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe dichloromethane mixture was filtered

출처 및 근거

ORD 기록
ord-edbd3762c9614a6f903d3ff06c27f6dd
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329159B2

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