Triethylamine → HCID 178491487, Verbindung

HRID 133794

Reaktionsgleichung

Reaktionsgleichung von HRID 133794
[OH:1][CH:2]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=O.[C:15]([NH:18][C:19]1[C:36]([Cl:37])=[CH:35][C:22]([CH2:23][NH:24]/[C:25](/[NH2:34])=[N:26]\[C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:21][C:20]=1[Cl:38])(=[O:17])[CH3:16].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl>[C:15]([NH:18][C:19]1[C:20]([Cl:38])=[CH:21][C:22]([CH2:23][NH:24]/[C:25](=[N:26]\[C:27](=[O:33])[O:28][C:29]([CH3:31])([CH3:32])[CH3:30])/[NH:34][C:4](=[O:6])[CH2:3][CH:2]([OH:1])[C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[CH:35][C:36]=1[Cl:37])(=[O:17])[CH3:16]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2724699PyBOPHCID 149273073-Hydroxy-3-(4-methoxyphenyl)propanoic acidHCID 178474312HCID 178474312, Verbindung

Produkt 1

HCID 178491487HCID 178491487, VerbindungAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-hydroxy-3-(4-methoxyphenyl)propanoic acid (13.7 mg, 0.07 mmol), (Z)-tert-butyl (4-acetamido-3,5-dichlorobenzylamino)(amino)-methylenecarbamate (26.3 mg), PyBop (36.4 mg), and triethylamine (0.01 mL) in dichloromethane (0.35 mL) was stirred at room temperature for 12 h. The crude reaction mixture was purified directly by preparative TLC eluting with 30% ethyl acetate/70% hexanes to give the title compound as a clear sticky oil (30 mg, 77% yield). 1H NMR (400 MHz, CDCl3) δ 1.48 (m, 9 H) 2.21 (s, 3 H) 2.70 (m, 2 H) 3.78 (m, 3 H) 4.55 (m, 2 H) 4.95 (m, 1 H) 6.80-7.00 (m, 3 H) 7.24-7.38 (m, 4 H), 9.10 (m, 1 H), 12.30 (m, 1 H). HPLC retention time: 2.493 min (method A). MS (ESI) (M+H)+ 553.08.

Aufarbeitung

  1. customThe crude reaction mixture
  2. customwas purified directly by preparative TLC
  3. washeluting with 30% ethyl acetate/70% hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e2bed52f21754bca906fd61d26a1a75a
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390925B2

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