Triethylamine → (2R,4R)-7-biphenyl-4-ylmethyl-2,4-dimethyl-6-oxo-nonanedioic acid 9-tert-butyl ester 1-ethyl ester

HRID 1945026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1945026
[C:1]([O:5][C:6](=[O:25])[CH2:7][CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[C:9](O)=[O:10])([CH3:4])([CH3:3])[CH3:2].[CH:26]1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.FC(F)(F)C(O)=O.[CH2:55]([O:57][C:58](=[O:65])[C@H:59]([CH3:64])[CH2:60][C@H:61](N)[CH3:62])[CH3:56].C(N(CC)CC)C>CN(C=O)C>[CH2:55]([O:57][C:58](=[O:65])[C@H:59]([CH3:64])[CH2:60][C@@H:61]([CH3:26])[CH2:62][C:9](=[O:10])[CH:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:25])[CH3:56]

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 596078262-Biphenyl-4-ylmethyl-succinic acid 4-tert-butyl esterHCID 86648194(2R,4R)-4-amino-2-methyl-pentanoic acid ethyl ester trifluoroacetate

Produkt 1

HCID 68424555(2R,4R)-7-biphenyl-4-ylmethyl-2,4-dimethyl-6-oxo-nonanedioic acid 9-tert-butyl ester 1-ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-biphenyl-4-ylmethyl-succinic acid 4-tert-butyl ester (100 mg, 0.29 mmol) in DMF (10 mL) is added HOBt (45 mg, 0.29 mmol) and EDCl (56 mg, 0.29 mmol) and the mixture is stirred at room temperature for 10 minutes then (2R,4R)-4-amino-2-methyl-pentanoic acid ethyl ester trifluoroacetate (47 mg, 0.29 mmol) and triethylamine (89 mg, 0.87 mmol) is added and the mixture is stirred at room temperature for 5 hours. The mixture is quenched with water and extracted with ethyl acetate. The organic layer is washed with water, brine, dried over magnesium sulfate and filtered. The solvent is removed under reduced pressure to give (2R,4R)-7-biphenyl-4-ylmethyl-2,4-dimethyl-6-oxo-nonanedioic acid 9-tert-butyl ester 1-ethyl ester.

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for 5 hours
  2. customThe mixture is quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1a1b0036b74e4b3f896dd7a0cd483775
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394853B2

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