Triethylamine → Fmoc-p-Me-D-Phe-OMe

HRID 324268

Reaktionsgleichung

Reaktionsgleichung von HRID 324268
[NH:1]([C:14]([O:16][CH2:17][CH:18]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]2[C:19]1=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[C@@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=C[C:39]=2N=N1.C(N(CC)CC)C>C(OCC)C.CO>[NH:1]([C:14]([O:16][CH2:17][CH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[C:30]1=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:15])[C@@H:2]([C:11]([O:13][CH3:39])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27560734-Methyl-D-phenylalanine, N-FMOC protected

Produkt 1

HCID 131722499Fmoc-p-Me-D-Phe-OMeAusbeute 108,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21864698Diethyl ether methanolLösungsmittel

Versuchsvorschrift

Fmoc—p—Me—D—Phe—OH (5 g) was dissolved in dichloromethane/methanol 9/1 v/v (50 ml). 2-(1H-benzotriazol-1-yl 1,1,3,3-tetramethyluronium tetrafluoroborate (4.4 g) was added and the solution adjusted to pH 8 by addition of triethylamine. The reaction mixture was stirred for 16 hours at room temperature. The mixture was washed successively with cold 1N hydrochloric acid solution, water, 5% sodium hydrogencarbonate, and water and dried over sodium sulphate. The filtrate was evaporated yielding 5.6 g of Fmoc—p—Me—D—Phe—OMe as an oil.

Aufarbeitung

  1. washThe mixture was washed successively with cold 1N hydrochloric acid solution, water, 5% sodium hydrogencarbonate, and water
  2. dry with materialdried over sodium sulphate
  3. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-d30abe3587df4b70acbe92223cfb77e6
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218365B1

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