2,2-Dimethyl-1,3-dioxane-4,6-dione → (R)-[1-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxane-5-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

HRID 491903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 491903
[C:1]([NH:8][C@@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:16][C:17]1([CH3:25])[O:24][C:22](=[O:23])[CH2:21][C:19](=[O:20])[O:18]1>ClCCl>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@H:9]([C:13]([CH:21]1[C:22](=[O:23])[O:24][C:17]([CH3:25])([CH3:16])[O:18][C:19]1=[O:20])=[O:15])[CH:10]([CH3:11])[CH3:12])([CH3:5])([CH3:6])[CH3:7]

Komponenten

4

Edukt 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acid

Produkt 1

HCID 58856323(R)-[1-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxane-5-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
3 °C

Versuchsvorschrift

A 5 L four-necked flask (equipped with mechanical stirrer, nitrogen inlet, thermocouple, and glass stopper) was charged with Boc-D-Valine (143.6 g, 0.661 mol) and dichloromethane (2.8 L). The reaction was chilled to ˜3° C. in an ice bath, and then 4-N,N-dimethylaminopyridine (124.6 g, 1.02 mol) and Meldrum's acid (104.8 g, 0.727 mol) were added to the reaction. To the reaction mixture was then added 1-[3-(dimethylaminopropyl)]-3-ethylcarbodiimide hydrochloride (EDCl, 139.4 g, 0.727 mol) over a five-minute period, and then the reaction mixture was allowed to warm to room temperature over 18 h (overnight). The reaction mixture washed with 5% (w/w) aqueous potassium bisulfate (4×600 mL), dried (MgSO4), and the solution was used directly in the next step without concentration or purification. A small portion was concentrated and displayed the following analytical data.

Aufarbeitung

  1. customA 5 L four-necked flask (equipped with mechanical stirrer, nitrogen inlet
  2. temperatureto warm to room temperature over 18 h (overnight)
  3. washThe reaction mixture washed with 5% (w/w) aqueous potassium bisulfate (4×600 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationthe solution was used directly in the next step without concentration or purification
  6. concentrationA small portion was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-d74dd21795f34a61bd3ea70a079ed615
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531545B2

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