Dimethylformamide → HCID 86656617, Verbindung

HRID 2036881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2036881
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:21]([OH:23])=O)[CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.C1C=CC2[N:37]([OH:38])N=NC=2C=1.[O:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]1NO>ClCCl.O.C(Cl)CCl.C(N(CC)CC)C>[O:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH:40]1[O:38][NH:37][C:21]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH2:12][N:11]([C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])[CH2:20][CH2:19]2)=[O:23]

Komponenten

9

Edukt 4

HCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 13168123Tetrahydropyranyl hydroxylamineHCID 58399186HCID 58399186, Verbindung

Produkt 1

HCID 86656617HCID 86656617, VerbindungAusbeute 96,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A mixture of 8.7 g 2-[(benzyloxy)carbonyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid, 94 ml DMF, 35 ml triethylamine, 4.1 g HOBt and 17 g EDC is stirred for 30 min at ambient temperature. 3.3 g of tetrahydropyran-2-yl-hydroxylamine are added and the reaction mixture is stirred overnight. The mixture is added to a mixture of 100 ml water and 200 ml dichloromethane. The organic phase is separated, washed, dried and evaporated. The crude product is purified by silica gel flash chromatography. 11.08 g of the title compound are obtained as colorless oil.

Aufarbeitung

  1. stirringthe reaction mixture is stirred overnight
  2. customThe organic phase is separated
  3. washwashed
  4. customdried
  5. customevaporated
  6. customThe crude product is purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bb057419571a4108a392c9c8eb4ba742
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575193B2

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