Phenethylamine → N1-(2-phenylethyl)-N2-[4-(trifluoromethyl)phenyl]-D-valinamide trifluoroacetate

HRID 1360382Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360382
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@@H:10]([C:14]([OH:16])=O)[CH:11]([CH3:13])[CH3:12])=[CH:5][CH:4]=1.[CH2:19]([NH2:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.C(N=C=NCCCN(C)C)C.[OH2:40].[OH:41]N1C2C=CC=CC=2N=N1>C(Cl)Cl>[F:1][C:2]([F:18])([F:17])[C:3]([OH:41])=[O:40].[C:21]1([CH2:20][CH2:19][NH:27][C:14](=[O:16])[C@@H:10]([CH:11]([CH3:12])[CH3:13])[NH:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:18])[F:17])=[CH:8][CH:7]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 1001PhenethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 13388455N-[4-(trifluoromethyl)phenyl]-D-valine

Produkt 1

HCID 86611433N1-(2-phenylethyl)-N2-[4-(trifluoromethyl)phenyl]-D-valinamide trifluoroacetateAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-[4-(Trifluoromethyl)phenyl]-D-valine (20 mg, 0.077 mmol) obtained in step 1, phenethylamine (11 μl, 0.087 mmol), 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (18 mg, 0.12 mmol) and 1-hydroxybenzotriazole monohydrate (22 mg, 0.12 mmol) were mixed in methylene chloride (3 mL), and the mixture was stirred overnight at room temperature. The solvent was evaporated and, using the following purification step A, the title compound (8.48 mg, 0.018 mmol, 23%) was obtained.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe following purification step A

Quellen und Nachweise

ORD-Eintrag
ord-b75bd82ac6fa4fb8aca1222070f6a819
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879863B2

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