HCID 68752536, compound → HCID 68751150, compound

HRID 333298Notes

Reaction equation

HRID 333298 reaction equation
C([O:8][C:9](=[O:41])[CH2:10][C:11]1([C:16]([NH:18][CH2:19][CH:20]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)=[CH:31][CH:30]=2)[C:21]([O:23]C(C)(C)C)=[O:22])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:9]([CH2:10][C:11]1([C:16]([NH:18][CH2:19][CH:20]([CH2:28][C:29]2[CH:30]=[CH:31][C:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=3)=[CH:33][CH:34]=2)[C:21]([OH:23])=[O:22])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1)([OH:41])=[O:8]

Participants

4

Reactant 1

HCID 68752536HCID 68752536, compound

Product 1

HCID 68751150HCID 68751150, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

Tert-Butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-2-(4-(pyridin-2-yl)benzyl)propanoate was dissolved in EtOAc (5 ml) and hydrogenated with 10% Pd/C under H2 at room temperature. After 3 hours, the reaction mixture was filtered and concentrated under reduced pressure. To the obtained residue in DCM (1.00 ml) at room temperature was added TFA, and the reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by reverse phase HPLC [5 to 35% ACN-water (0.1°/oTFA) over 10 min by X-bridge phenyl column] to give the title compound (48 mg). LCMS (condition A): 411.3 (M+1); retention time=1.24 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.44-1.62 (m, 6H), 1.96-2.06 (m, 2H), 2.59 (dd, J=18.7, 16.4 Hz, 2H), 2.74-2.91 (m, 3H), 3.14-3.24 (m, 1H), 3.24-3.33 (m, 1H), 7.34 (d, J=8.3 Hz, 2H), 7.47-7.53 (m, 1H), 7.68 (t, J=5.6 Hz, 1H), 7.96 (d, J=8.3 Hz, 2H), 8.03-8.11 (m, 2H), 8.68-8.74 (m, 1H).

Workup

  1. filtrationthe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. additionTo the obtained residue in DCM (1.00 ml) at room temperature was added TFA
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. customThe obtained residue was purified by reverse phase HPLC [5 to 35% ACN-water (0.1°/oTFA) over 10 min by X-bridge phenyl column]

Sources & evidence

ORD record
ord-2f80cfff70054efc85f1fc0a58eb67b2
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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