Triethylamine → 2-(3-bromophenoxy)-N-(cyanomethyl)-4-methylpentanamide

HRID 1744062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744062
[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][CH:6]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:7]([O:9]C)=O.[Li].Cl.[NH2:20][CH2:21][C:22]#[N:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>O.Cl.CN(C=O)C.C(OCC)(=O)C.O1CCCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][CH:17]=1)[O:5][CH:6]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:7]([NH:23][CH2:22][C:21]#[N:20])=[O:9]

Komponenten

12

Edukt 5

HCID 8471TriethylamineHCID 3028194LithiumHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11491918Aminoacetonitrile hydrochlorideHCID 22235997Methyl 2-(3-bromophenoxy)-4-methylpentanoate2×

Produkt 1

HCID 222357482-(3-bromophenoxy)-N-(cyanomethyl)-4-methylpentanamide

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 2-(3-bromophenoxy)-4-methylpentanoate, in a mixture of water (42 mL), methanol (8 mL) and tetrahydrofuran (4 mL) was treated with lithium hydroxyde monohydrate (1.3 g, 31.6 mmoles) until disappearance of the starting material was observed by TLC. The reaction was diluted with 1.2 N hydrochloric acid until pH 1. The aqueous phase was extracted 3 times with dichloromethane. The organic phase was concentrated under reduced pressure to provide a residue that was used as such in the next reaction. To a solution of the resulting crude 2-(3-bromophenoxy)-4-methylpentanoic acid in DMF (30 mL) was added aminoacetonitrile hydrochloride (2.9 g, 31.5 mmoles) and HATU (6.3 g, 16.5 mmoles). After stirring for 1 minute, triethylamine (8.75 mL, 63 mmoles) was added in one portion. The reaction was stirred overnight, diluted with ethyl acetate and water. The organic phase was separated and washed twice with 1.2 N hydrochloric acid, brine and dried over magnesium sulfate. After concentration under reduced pressure, the solid 2-(3-bromophenoxy)-N-(cyanomethyl)-4-methylpentanamide obtained was sufficiently pure.

Aufarbeitung

  1. extractionThe aqueous phase was extracted 3 times with dichloromethane
  2. concentrationThe organic phase was concentrated under reduced pressure
  3. customto provide a residue that
  4. customsuch in the next reaction
  5. stirringThe reaction was stirred overnight
  6. customThe organic phase was separated
  7. washwashed twice with 1.2 N hydrochloric acid, brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationAfter concentration under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f3de916254d44b6cb5f986f407287d8c
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012075B2

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