Triethylamine → HCID 178440879, Verbindung

HRID 1988362Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1988362
[C:1]([C:5]1[CH:6]=[C:7](C(C)C(O)=O)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[NH2:23][CH2:24][C:25]1[CH:26]=[C:27]([NH:31][C:32]([C:34]2[S:35][CH:36]=[CH:37][CH:38]=2)=[NH:33])[CH:28]=[CH:29][CH:30]=1.[OH:39]N1C2C=CC=CC=2N=N1.Cl.CN(C)[CH2:52][CH2:53][CH2:54]N=C=NCC.CCN(CC)CC>C(Cl)Cl.O>[C:12]([C:9]1[CH:8]=[C:7]([CH2:54][CH2:53][C:52]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][C:32](=[NH:33])[C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)[CH:26]=2)=[O:39])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]=1[OH:11])([CH3:15])([CH3:14])[CH3:13]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21692686HCID 21692686, VerbindungHCID 178478771HCID 178478771, Verbindung

Produkt 1

HCID 178440879HCID 178440879, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 2.78 g (10 mmol) of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid, 3.04 g (10 mmol) of N-[3-(aminomethyl)phenyl]thiophene-2-carboximidamide 2HCl (J. Med. Chem. (1998), 41(15), 2858), 1.48 g (11 mmol) of 1-hydroxybenzotriazole in 100 ml of CH2Cl2, in a 250 ml flask, 4.21 g (22 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 6.1 ml (44 mmol) of Et3N were added. After overnight stirring at 20° C., the reaction mixture was diluted with 100 ml water, stirred and decanted. The organic layer was successively washed with NaHCO3 saturated solution, water, KHSO4, (1M), water and brine. After drying over Na2SO4 and filtration, the organic solution was concentrated under reduced pressure. The residue was flash chromatographed over silica gel, using heptane/EtOAc:1/1 as eluent, to yield a cream light solid (85%). Melting point: 163-164° C.

Aufarbeitung

  1. stirringstirred
  2. customdecanted
  3. washThe organic layer was successively washed with NaHCO3 saturated solution, water, KHSO4, (1M), water and brine
  4. dry with materialAfter drying over Na2SO4 and filtration
  5. concentrationthe organic solution was concentrated under reduced pressure
  6. customchromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-ddf76202f0374363987b8f3393f19969
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553976B2

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