Triethylamine → HCID 43401847, Verbindung

HRID 1891268Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1891268
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][NH:7][CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:21]1([NH2:24])[CH2:23][CH2:22]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.CCOC(C)=O.CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][CH2:8][C:9]([NH:24][CH:21]2[CH2:23][CH2:22]2)=[O:11])=[CH:12][CH:13]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 2724699PyBOPHCID 28354373N-[(4-Bromophenyl)methyl]glycine

Produkt 1

HCID 43401847HCID 43401847, VerbindungAusbeute 30,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21584119Ethylacetate methanolLösungsmittel

Versuchsvorschrift

To a suspension of 2-(4-bromobenzylamino)acetic acid (7H2) (109 mmol, 26.5 g) in dichloromethane (300 ml) was added triethylamine (326 mmol, 33.0 g), cyclopropylamine (7H3) (163 mmol, 9.30 g) and PyBOP (109 mmol, 56.5 g). The suspension was stirred at room temperature overnight before concentration and purification on silica eluting with EtOAc/MeOH 1:0 to 9:1 to give 2-(4-bromobenzylamino)-N-cyclopropylacetamide (7H4) 9.38 g (30.3%); 1H NMR (400 MHz, MeODd4) 7.57 (d, 2H) 7.34 (d, 2H) 4.13 (m, 2H) 3.63 (s, 2H) 2.68 (m 1H) 0.76 (m, 2H) 0.56 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-7910d7f7306b4ee59c5944fdde9c0e37
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507521B2

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