Phenethylamine → 1307953-73-6

HRID 334003

Reaktionsgleichung

Reaktionsgleichung von HRID 334003
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OC([NH:20][C@@H:21]([C:23](O)=[O:24])[CH3:22])=O)C1C=CC=CC=1.Cl.C(N=C=NCCCN(C)C)C.C1C2C(=CC(S(Cl)(=O)=O)=CC=2)C=CN=1>ClCCl.[C].[Pd]>[NH2:20][C@H:21]([CH3:22])[C:23]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:24]

Komponenten

7

Edukt 4

HCID 1001PhenethylamineHCID 70832N-Cbz-d-alanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 55280287Isoquinoline-6-sulfonyl chloride

Produkt 1

HCID 109137881307953-73-6Ausbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418390HCID 178418390, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Phenethylamine (285 mg) and N-(benzyloxycarbonyl)-D-alanine (500 mg) were condensed (618 mg, 85%) using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (472 mg) in dichloromethane. (R)-2-amino-N-phenethylpropanamide (197 mg) obtained by further hydrogenation reaction in the presence of 10% palladium-carbon, and isoquinoline-6-sulfonyl chloride prepared in Reference Example 1 were condensed (237 mg, 60%) in the presence of triethylamine (0.284 mL) in dichloromethane. Subsequently, 40 mg of the title compound was obtained as a pale yellow solid (13%) with reference to the method of Step 3 of Example 1.

Aufarbeitung

  1. customcondensed (618 mg, 85%)

Quellen und Nachweise

ORD-Eintrag
ord-80a3c77f7b164a1d9c7b22b5197614d3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883792B2

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