HCID 68750672, compound → HCID 68750602, compound

HRID 333297Notes

Reaction equation

HRID 333297 reaction equation
C([O:8][C:9](=[O:41])[CH2:10][C:11]1([NH:16][C:17](=[O:40])[CH:18]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[CH:30][CH:29]=2)[CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH2:15][CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:31]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:30]=[CH:29][C:28]([CH2:27][CH:18]([C:17]([NH:16][C:11]2([CH2:10][C:9]([OH:41])=[O:8])[CH2:12][CH2:13][CH2:14][CH2:15]2)=[O:40])[CH2:19][C:20]([OH:22])=[O:21])=[CH:33][CH:32]=1

Participants

4

Reactant 1

HCID 68750672HCID 68750672, compound

Product 1

HCID 68750602HCID 68750602, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

Tert-butyl 4-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentylamino)-3-(biphenyl-4-ylmethyl)-4-oxobutanoate was dissolved in EtOAc (6 mL) and hydrogenated with 10% Pd/C at room temperature under hydrogen. After 2 hr, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in DCM, and to the mixture was added TFA. After stirred at room temperature for 1.5 hr, the reaction mixture was concentrated under reduced pressure. The obtained residue was purified by reverse phase HPLC [40 to 75% ACN-water (0.1% TFA) over 10 min by Sunfire C18 column] to give the title compound (23 mg). LCMS (condition B): 410.1 (M+1); retention time=0.99 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38-1.61 (m, 6H), 1.95-2.05 (m, 2H), 2.10 (dd, J=16.4, 5.8 Hz, 1H), 2.41-2.49 (m, 1H), 2.57 (dd, J=12.9, 7.1 Hz, 1H), 2.73 (dd, J=35.4, 14.7 Hz, 2H), 2.82-2.99 (m, 2H), 7.29 (d, J=8.1 Hz, 2H), 7.34 (t, J=7.3 Hz, 1H), 7.45 (t, J=7.7 Hz, 2H), 7.56 (d, J=8.3 Hz, 2H), 7.63 (d, J=7.1 Hz, 3H), 11.97 (br. s., 2H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe obtained residue was dissolved in DCM
  3. additionto the mixture was added TFA
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customThe obtained residue was purified by reverse phase HPLC [40 to 75% ACN-water (0.1% TFA) over 10 min by Sunfire C18 column]

Sources & evidence

ORD record
ord-54a13933cb4944a9b1e2229155c2f35c
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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