Phenylacetic Acid → HCID 59371317, compound

HRID 2095426Notes

Reaction equation

HRID 2095426 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25]O)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH2:25][O:9][C:8](=[O:10])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 999Phenylacetic AcidHCID 10868DicyclohexylcarbodiimideHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 59371317HCID 59371317, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of phenylacetic acid (327 mg, 2.40 mmol, 1.2 equiv.) and 1-(tert-butoxycarbonyl)-4-(2-hydroxyethyl)piperidine (459 mg, 2.00 mmol) in CH2Cl2 (10 mL) were added DCC (495 mg, 2.40 mmol, 1.2 equiv.) and DMAP (12.2 mg, 100 μmol, 0.1 equiv.). The reaction mixture was allowed to stand overnight. After filtration, the liquid phase was washed with brine and dried over Na2SO4. After the solvent was removed, the residue was purified by CC (SiO2, hexane/EtOAc 4:1). The ester (672 mg, 97%) was obtained as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 7.31 (m, 5H), 4.14 (t, 2H, J=6.8 Hz), 4.03 (d, 2H, J=13.2 Hz), 3.61 (s, 2H), 2.60 (dt, 2H, J=2.0, 12.8 Hz), 1.56 (m, 5H), 1.45 (s, 9H), 1.06 (m, 2H).

Workup

  1. filtrationAfter filtration
  2. washthe liquid phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter the solvent was removed
  5. customthe residue was purified by CC (SiO2, hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-06ac1a6511d84e4d86e91e5efa655b1d
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

Loading…