Dimethylformamide → (R)-tert-butyl 2-(3-cyclopentylureido)-2-phenylacetate

HRID 68271

Reaktionsgleichung

Reaktionsgleichung von HRID 68271
Cl.[NH2:2][C@H:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]([OH:6])=[O:5].CCN([CH:19]([CH3:21])[CH3:20])C(C)C.[CH:22]1([N:27]=[C:28]=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23]1.[CH3:30]N(C=O)C>>[CH:22]1([NH:27][C:28](=[O:29])[NH:2][C@H:3]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([O:6][C:19]([CH3:21])([CH3:30])[CH3:20])=[O:5])[CH2:26][CH2:25][CH2:24][CH2:23]1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 643500Cyclopentyl IsocyanateHCID 12238435(R)-2-Amino-2-phenylacetic acid hydrochloride

Produkt 1

HCID 59166526(R)-tert-butyl 2-(3-cyclopentylureido)-2-phenylacetate

Versuchsvorschrift

To a stirred solution of (R)-2-amino-2-phenylacetic acid hydrochloride (1.0 g, 4.10 mmol) and Hunig's base (1.0 mL, 6.15 mmol) in DMF (15 mL) was added cyclopentyl isocyanate (0.46 mL, 4.10 mmol) dropwise and over 10 minutes. After stirring at room temperature for 3 hours, the reaction was concentrated under reduced pressure and the resulting residue was traken up in ethyl acetate. The organic layer was washed with H2O and brine, dried (MgSO4), filtered, and concentrated under reduced pressure. (R)-tert-butyl 2-(3-cyclopentylureido)-2-phenylacetate was obtained as an opaque oil (1.32 g; 100%) and used without further purification. 1H NMR (500 MHz, CD3Cl-D) δ ppm 1.50-1.57 (m, 2H) 1.58-1.66 (m, 2H) 1.87-1.97 (m, 2H) 3.89-3.98 (m, 1H) 5.37 (s, 1H) 7.26-7.38 (m, 5H). LCMS: Anal. Calcd. for C18H26N2O3 318.19 found 319.21 (M+H)+; HPLC XTERRA C-18 3.0×50 mm, 0 to 100% B over 4 minutes, 1 minute hold time, A=90% water, 10% methanol, 0.1% TFA, B=10% water, 90% methanol, 0.1% TFA, RT=2.82 min, 96% homogeneity index.

Aufarbeitung

  1. concentrationthe reaction was concentrated under reduced pressure
  2. washThe organic layer was washed with H2O and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2c6b273138514945afadfd848e27c3bc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822444B2

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