Triethylamine → ((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl ester

HRID 446947Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446947
O.[C:2]([NH:9][C@@H:10]([C:15]([OH:17])=O)[CH2:11][CH:12]([CH3:14])[CH3:13])([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].[CH2:18]([N:20](CC)[CH2:21]C)C.Cl.CNC.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[C:5]([O:4][C:2](=[O:3])[NH:9][C@@H:10]([C:15](=[O:17])[N:20]([CH3:21])[CH3:18])[CH2:11][CH:12]([CH3:14])[CH3:13])([CH3:8])([CH3:7])[CH3:6]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2724699PyBOPHCID 2724763D-Leucine, N-[(1,1-dimethylethoxy)carbonyl]-, monohydrate

Produkt 1

HCID 28165661((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl esterAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of Boc-D-leucine monohydrate (2.0 g, 8.0 mmol), triethylamine (5.6 mL, 40.1 mmol), and dimethylamine hydrochloride (1.31 g, 16.0 mmol) in DMF (15 mL) at room temperature was added PyBOP (4.59 g, 8.82 mmol). The reaction mixture was stirred overnight then diluted with EtOAc (50 mL) and washed with water (4×50 mL). The combined organic extracts were dried (Na2SO4) and evaporated under vacuum. The crude residue was purified by SiO2 chromatography (80 g, hexanes/EtOAc, 1:1) to give 1.19 g (58%) of ((R)-1-dimethylcarbamoyl-3-methyl-butyl)-carbamic acid tert-butyl ester as a colorless viscous oil.

Aufarbeitung

  1. washwashed with water (4×50 mL)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. customevaporated under vacuum
  4. customThe crude residue was purified by SiO2 chromatography (80 g, hexanes/EtOAc, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-948d16f949124e3abb92073d9e0fda0f
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08481541B2

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