Triethylamine → 5-(2-(9H-fluoren-9-ylidene)acetamido)pentanoic acid methyl ester

HRID 1926186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1926186
[CH:1]1[C:13]2[C:12](=[CH:14][C:15](O)=[O:16])[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.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.Cl.[CH3:48][O:49][C:50](=[O:56])[CH2:51][CH2:52][CH2:53][CH2:54][NH2:55]>[Cl-].[Na+].O.CN(C=O)C>[CH3:48][O:49][C:50](=[O:56])[CH2:51][CH2:52][CH2:53][CH2:54][NH:55][C:15](=[O:16])[CH:14]=[C:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 967929H-Fluoren-9-ylideneacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13672034Methyl 5-aminopentanoate hydrochlorideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 579720535-(2-(9H-fluoren-9-ylidene)acetamido)pentanoic acid methyl esterAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

2-(9H-fluoren-9-ylidene)acetic acid (222 mg, 1 mmol) and 8 ml of DMF were stirred at room temperature while 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (394 mg, 2 mmol), hydroxybenzo-triazole (162 mg, 1.2 mmol), triethylamine (404 mg, 4 mmol) and 5-aminovaleric acid methyl ester hydrochloride (202 mg, 1.2 mmol) were added. The mixture was stirred for 24 hours at room temperature. The mixture was diluted with 400 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (278 mg, 68% yield) as a white solid. LC-MS (m/z) 336 (M+1).

Aufarbeitung

  1. additionwere added
  2. filtrationThe solids were collected by vacuum filtration
  3. washwashed with water
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-a479601e4d144f0a8d5655deb5928ce7
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08178577B2

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