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

HRID 1484245Notes

Reaction equation

HRID 1484245 reaction equation
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

Participants

5

Reactant 4

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

Product 1

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

Procedure

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 taken 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 minutes 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.

Workup

  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

Sources & evidence

ORD record
ord-473daa01349f4fd48c5f3806f3825cff
Source dataset
uspto-grants-2016_08
Patent number
US09421192B2

Reaction notes

Loading…