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

HRID 1471079Notes

Reaction equation

HRID 1471079 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, CD3C1-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.

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-7125fafe220f46d8a9eb7b359935415d
Source dataset
uspto-grants-2015_04
Patent number
US09006455B2

Reaction notes

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