Triethylamine → 2-Ethynyl-3'',4''-dimethoxy-biphenyl-4-carboxylic acid (1-methyl-4-pyridin-3-yl-butyl)-amide

HRID 2073300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2073300
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([C:17](O)=[O:18])=[CH:13][C:12]=2[C:20]#[CH:21])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:46][C@@H:47]([NH2:57])[CH2:48][CH2:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1>CN(C)C=O.C(OCC)(=O)C>[C:20]([C:12]1[CH:13]=[C:14]([C:17]([NH:57][C@H:47]([CH3:46])[CH2:48][CH2:49][CH2:50][C:51]2[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=2)=[O:18])[CH:15]=[CH:16][C:11]=1[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)#[CH:21]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 11062727(R)-2-Amino-5-(3-pyridyl)pentaneHCID 145701343',4'-Dimethoxy-2-ethynyl[1,1'-biphenyl]-4-carboxylic acid

Produkt 1

HCID 145701032-Ethynyl-3'',4''-dimethoxy-biphenyl-4-carboxylic acid (1-methyl-4-pyridin-3-yl-butyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 459 mg of 3',4'-dimethoxy-2-ethynyl[1,1'-biphenyl]-4-carboxylic acid in 8 mL of dimethylformamide was cooled in an ice bath and treated with 0.25 mL of triethylamine and 0.38 mL of diphenylphosphoryl azide. After 1 hour. 0.3 mL of (R)alpha-methyl-3-pyridinebutanamine was added and the reaction mixture was allowed to warm to room temperature over 48 hours. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried and concentrated. The residue was chromatographed over 50 g of silica gel eluting with ethyl acetate and the product was crystallized from ethyl acetate-hexane to give 576 mg of (R)-2-Ethynyl-3',4'-dimethoxy-N-[1-methyl-4-(3-pyridinyl)butyl][1.1'-biphenyl]-4-carboxamide, mp 135°-137° C.

Aufarbeitung

  1. washwashed with water and brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was chromatographed over 50 g of silica gel eluting with ethyl acetate
  5. customthe product was crystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ce066783a42247559d200bdd11fbcd1e
Quelldatensatz
uspto-grants-1990_04
Patentnummer
US04916145

Notizen zur Reaktion

Wird geladen…