Benzylamine → (s)-2-(2-Benzylamino-5-trifluoromethyl-benzoylamino)-butyric acid tert-butyl ester

HRID 1987881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1987881
[C:1]([O:5][C:6](=[O:24])[C@@H:7]([NH:10][C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1Cl)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC(C(F)(F)F)=CC=1C(O)=O.N[C@@H](CC)C(OC(C)(C)C)=O.[CH2:50]([NH2:57])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1.[Cl-].[NH4+].[Cu].[Cu]Br>[C:1]([O:5][C:6](=[O:24])[C@@H:7]([NH:10][C:11](=[O:23])[C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:13]=1[NH:57][CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[CH2:8][CH3:9])([CH3:4])([CH3:3])[CH3:2]

Komponenten

10

Edukt 5

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 6881822-Chloro-5-(trifluoromethyl)benzoic acidHCID 7019938(2S)-2-amino butanic acid t-butyl esterHCID 66593952(s)-2-(2-Chloro-5-trifluoromethyl-benzoylamino)-butyric acid tert-butyl ester

Produkt 1

HCID 57725377(s)-2-(2-Benzylamino-5-trifluoromethyl-benzoylamino)-butyric acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23978CopperKatalysatorHCID 24593copper(I) bromideKatalysatorHCID 84541-MethylpyrrolidineLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a solution of (S)-2-(2-chloro-5-trifluoromethyl-benzoylamino)-butyric acid tert-butyl ester (prepared from 2-chloro-5-trifluoromethylbenzoic acid and (S)-2-aminobutyric acid, tert butyl ester in a procedure similar to that described in method F) (3 g) and benzylamine (1.1 ml) in N-methylpyrolidine (40 ml) was added potassium carbonate (1.6 g), copper (30 mg) and copper (I) bromide (15 mg). The mixture was heated at 160° C. for 3 hours then cooled to room temp. and diluted with saturated ammonium chloride solution. The mixture was extracted with ethyl acetate and the organic solution dried (magnesium sulfate), filtered and concentrated. The residue was purified on silica gel, eluting with 15% ethyl acetate/hexane. The sub-titled product was obtained as a white solid (950 mg, 27%). 1H NMR (400 MHz, CDCl3) δ 1.04 (3H, t), 1.50 (9H, s), 2.86 (1H, m), 2.02 (1H, m), 4.50 (2H, d), 4.65 (1H, m), 6.69 (2H, m), 7.21-7.70 (7H, m), 8.42 (1H, m) ppm; MS ES(−) 435.32 (M−H).

Aufarbeitung

  1. temperaturethen cooled to room temp.
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialthe organic solution dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel
  7. washeluting with 15% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-8a9b9600376648a1b2f5618bd22f510d
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07553852B2

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