1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67174569, Verbindung

HRID 85387Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 85387
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C:13]([NH:20][CH2:21][C:22](O)=[O:23])([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].CCN=C=NCCCN(C)C.CN(C1C=CC=CN=1)C>ClCCl>[C:16]([O:15][C:13]([NH:20][CH2:21][C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:23])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 135127Methyl 5-amino-2-hydroxybenzoate

Produkt 1

HCID 67174569HCID 67174569, VerbindungAusbeute 46,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of methyl 5-amino-2-hydroxybenzoate (1.5 g, 9.0 mmol) in dichloromethane (50 mL) was added BOC-glycine (1.57 g, 9.0 mmol), EDCI (1.89 g, 9.9 mmol) and dimethylaminopyridine (0.11 g, 0.9 mmol). The reaction was stirred (RT, 2.5 h), and then partitioned between CH2Cl2 and brine. The aqueous layer was extracted with CH2Cl2 and the combined organic layers were washed with brine and dried over MgSO4. The crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2) to afford methyl 5-(2-(tert-butoxycarbonylamino)-acetamido)-2-hydroxybenzoate (1.37 g). Mass calculated for C15H20N2O6=324.33; found: [M+Na]+=347.2.

Aufarbeitung

  1. custompartitioned between CH2Cl2 and brine
  2. extractionThe aqueous layer was extracted with CH2Cl2
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customThe crude product was purified by silica gel chromatography (0-5% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-b6444861daa34fc8b2564d34ff2bfe6b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846972B2

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