Trifluoroacetic acid → HCID 59166508, compound

HRID 1919199Notes

Reaction equation

HRID 1919199 reaction equation
[CH3:1][N:2]([CH3:20])[C:3](=[O:19])[NH:4][C@H:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([O:8]C(C)(C)C)=[O:7].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][N:2]([CH3:20])[C:3](=[O:19])[NH:4][C@H:5]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59166445(R)-tert-butyl 2-(3,3-dimethylureido)-2-phenylacetate

Product 1

HCID 59166508HCID 59166508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ((R)-tert-butyl 2-(3,3-dimethylureido)-2-phenylacetate (0.86 g, 3.10 mmol) in CH2Cl2 (250 mL) was added TFA (15 mL) dropwise and the resulting solution was stirred at rt for 3 hours. The desired compound was then precipitated out of solution with a mixture of EtOAC:Hexanes (5:20), filtered off and dried under reduced pressure. (R)-2-(3,3-dimethylureido)-2-phenylacetic acid was isolated as a white solid (0.59 g, 86%) and used without further purification. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.82 (s, 6H) 5.22 (d, J=7.32 Hz, 1H) 6.58 (d, J=7.32 Hz, 1H) 7.28 (t, J=7.17 Hz, 1H) 7.33 (t, J=7.32 Hz, 2H) 7.38-7.43 (m, 2H) 12.65 (s, 1H). LCMS: Anal. Calcd. for C11H14N2O3: 222.24. Found: 223.21 (M+H)+. HPLC XTERRA® C-18 3.0×50 mm, 0 to 100% B over 2 minutes, 1 minute hold time, A=90% water, 10% methanol, 0.2% H3PO4, B=10% water, 90% methanol, 0.2% H3PO4, RT=0.75 min, 93% homogeneity index.

Workup

  1. customThe desired compound was then precipitated out of solution with a mixture of EtOAC
  2. filtrationHexanes (5:20), filtered off
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-9aeb99b292ed4477b6aa45b480389940
Source dataset
uspto-grants-2013_12
Patent number
US08618153B2

Reaction notes

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