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

HRID 2035365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2035365
[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

Komponenten

8

Edukt 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

Produkt 1

HCID 59668673HCID 59668673, VerbindungAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-700c39fa677b4b619ab1a634231ac34e
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08574563B2

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