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4-Methylmorpholine → N1-[1(RS)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]-L-leucinamide

HRID 850876
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 850876
C(OC(CCC(N[C@H](C(N[C@H](C([NH:37][C@H:38]([C:47]([NH:49][C@H:50](C(N[C@H](C(O)=O)CC(C)C)=O)[C:51]([CH3:54])(C)C)=[O:48])[CH2:39][C:40]1[CH:45]=CC=C[C:41]=1C)=O)CCC(=O)OC(C)(C)C)=O)CC(=O)OC(C)(C)C)=O)=O)(C)(C)C.CN1CCOCC1.ClC(OCC(C)C)=O.FC(F)(F)C(O)=O.C(C([B:92]1[O:96][C:95]([CH3:98])([CH3:97])[C:94]([CH3:100])([CH3:99])[O:93]1)N)C>CN(C)C=O.ClCCl>[CH3:99][C:94]1([CH3:100])[C:95]([CH3:98])([CH3:97])[O:96][B:92]([CH:50]([NH:49][C:47](=[O:48])[C@H:38]([CH2:39][CH:40]([CH3:41])[CH3:45])[NH2:37])[CH2:51][CH3:54])[O:93]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 19364709a-(RS)-ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-methylamine trifluoroacetateHCID 22942121N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-alpha-aspartyl]-O-tert-butyl-L-alpha-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucine

Produkt 1

HCID 131721619
N1-[1(RS)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]-L-leucinamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

0.25 g (0.27 mmol) of N-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-L-leucine was dissolved in 2 ml of dimethylformamide and 5 ml of dichloromethane. 0.15 ml (1.6 mmol) of N-methylmorpholine was added and the solution was cooled to -15° C. under a nitrogen atmosphere. 50 mg (0.38 mmol) of isobutyl chloroformate were added and the solution was stirred for 10 minutes at -15° C. 0.1 g (0.33 mmol) of α-(RS)-ethyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-methylamine trifluoroacetate was added and the mixture was stirred at room temperature for 18 hours. After evaporation the residue was partitioned between ethyl acetate and 2M hydrochloric acid. The organic layer was washed with 2M hydrochloric acid, water and saturated sodium chloride solution and then dried over anhydrous sodium sulphate. After evaporation there was obtained 0.26 g of N2-N-[N-[N-[N-[3-(tert-butoxycarbonyl)propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-N1-[1(RS)-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propyl]-L-leucinamide in the form of a solid; MS: m/e 1085 [M+H].

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. customAfter evaporation the residue
  3. customwas partitioned between ethyl acetate and 2M hydrochloric acid
  4. washThe organic layer was washed with 2M hydrochloric acid, water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. customAfter evaporation

Quellen und Nachweise

ORD-Eintrag
ord-563a59da049a40c6b865aa452206cf2d
Quelldatensatz
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06018020

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