HCID 58674965, compound → HCID 58674957, compound

HRID 1809479Notes

Reaction equation

HRID 1809479 reaction equation
[C:1]([O:5][C:6](=[O:33])[C@@H:7]([N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH:21]C(OCC2C=CC=CC=2)=O)[C:16]1=[O:32])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CO.CCOC(C)=O.[Pd]>[C:1]([O:5][C:6](=[O:33])[C@@H:7]([N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([NH2:21])[C:16]1=[O:32])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 58674965HCID 58674965, compound

Product 1

HCID 58674957HCID 58674957, compoundYield 92.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-2-(3-benzyloxycarbonylamino-2-oxo-2H-pyridin-1-yl)-3-phenyl-propionic acid tert-butyl ester (4 g, 8.92 mmol) in a mixture of MeOH (40 mL) and EtOAc (10 mL) was added 10% Pd/C (500 mg). The mixture was degassed and stirred at room temperature for 4 hours under an atmosphere of hydrogen (balloon pressure). The reaction mixture was filtered through a short pad of celite which was then flushed with MeOH. The combined filtrates were evaporated under reduced pressure to afford the title compound as a white solid (2.6 g, 92%); 1H NMR (400 MHz, CDCl3) δ 1.48 (9H, s), 3.32 (1H, dd), 3.52 (1H, dd), 3.95 (2H, br s), 5.55 (1H, dd), 6.00 (1H, t), 6.55 (1H, d), 6.72 (1H, d), 7.18-7.35 (5H, m).

Workup

  1. customThe mixture was degassed
  2. filtrationThe reaction mixture was filtered through a short pad of celite which
  3. customwas then flushed with MeOH
  4. customThe combined filtrates were evaporated under reduced pressure

Sources & evidence

ORD record
ord-7fe7418b16164b70bd92f05b50af0115
Source dataset
uspto-grants-2013_01
Patent number
US08362043B2

Reaction notes

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