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Benzyl chloroformate → Methyl 2-(2-(((benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoate

HRID 627578
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 627578
[Cl-].[CH3:2][O:3][C:4](=[O:18])[CH:5]([NH:10][C:11](=[O:17])[CH:12]([NH3+:16])[CH2:13][C:14]#[CH:15])[CH2:6][CH:7]([CH3:9])[CH3:8].CCN(C(C)C)C(C)C.[CH2:28]([O:35][C:36](Cl)=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[CH2:28]([O:35][C:36]([NH:16][CH:12]([CH2:13][C:14]#[CH:15])[C:11]([NH:10][CH:5]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:4]([O:3][CH3:2])=[O:18])=[O:17])=[O:37])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 900103681-((1-Methoxy-4-methyl-1-oxopentan-2-yl)amino)-1-oxopent-4-yn-2-aminium chloride

Produkt 1

HCID 78106115Methyl 2-(2-(((benzyloxy)carbonyl)amino)pent-4-ynamido)-4-methylpentanoateAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of compound 2 (8.5 g; 31 mmol) in dry THF (100 mL) was added DIEA (16.02 g; 124 mmol) and the reaction mixture was stirred for 30 min at room temperature. Benzylchloroformate (6.87 g; 40.3 mmol) was added and stirring was continued at room temperature for 16 h. The solvent was removed on the rotary evaporator and the residue was taken up in ethyl acetate (150 mL) and washed sequentially with water (50 mL), 5% HCl (2×50 mL), and brine (50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give 3 as a white solid (10.46 g: 90% yield). 1H NMR (CDCl3) δ 7.3 (m, 5H), 6.7 (s, 1H), 5.6 (s, 1H), 5.1 (s, 2H), 4.6 (m, 1H), 4.4 (m, 1H), 3.7 (s, 3H), 2.6 (m, 2H), 2.8 (s, 1H), 2.6 (m, 1H), 1.6 (m, 2H), 1.5 (m, 1H), 0.9 (d, 6H).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at room temperature for 16 h
  3. customThe solvent was removed on the rotary evaporator
  4. washwashed sequentially with water (50 mL), 5% HCl (2×50 mL), and brine (50 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-74690623dbbd45ab9e778fee6483639e
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09309284B2

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