1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59668673、化合物

HRID 1873892ノート

反応式

HRID 1873892 の反応式
[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

参加物

8

反応物 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

生成物 1

HCID 59668673HCID 59668673、化合物収率 102%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-81101fa32fe848b88e0804d0a19837af
出典データセット
uspto-grants-2012_11
特許番号
US08303944B2

反応ノート

読み込み中…