HCID 57956922, compound → Compound 20

HRID 553067Notes

Reaction equation

HRID 553067 reaction equation
C([O:8][C:9](=[O:38])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:37])[CH2:16][CH2:17][C:18](=[O:36])[C@@H:19]([NH:27][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.CO.[Pd]>[C:28]([NH:27][C@@H:19]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:18](=[O:36])[CH2:17][CH2:16][C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:38])=[O:8])=[O:37])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 57956922HCID 57956922, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 156271Compound 20

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a stirred solution of the (5S)-5-[(N-benzoyl)amino]-4-oxo-6-phenyl-hexanoyl-L-proline benzyl ester (100 mg, 0.1951 mmol) in dry EtOAc-MeOH (3:1 ratio) (10 mL) was added 10% Pd/C (100 mg) and the resulting mixture stirred at room temperature under 1 atmosphere of hydrogen for 24 h. Filtration of the black Pd residue and evaporation of the filtrate gave a pale yellow crude residue. Column chromatography on silica gel elution with 37% MeOH-EtOAc afforded the (5S)-5-[(N-benzoyl)amino]-4-oxo-6-phenyl-hexanoyl-L-proline 5a as a white solid powder (68 mg, 82%): mp 148-149° C. (lit.12 mp 151-153° C.); Rf 0.28 (37% MeOH-EtOAc); IR (KBr) ν 1765 (CO), 3300 (broad, COOH) cm−1; 1H NMR (300 MHz, CD3OD) δH 2.01 (2H, m, —CH2), 2.51 (4H, m, —CH2CO and —CH2CH2N), 2.78 (2H, m, —CH2CO), 3.02-3.38 (4H, m —CH2Ph and —CH2N—), 4.84 (1H, m, —CH—), 4.98 (1H, m, —CH—) and 7.08-7.68 (10H, m, Ar—H); 13C NMR (75 MHz, CD3OD) δC 22.6, 24.5, 28.6, 34.3, 36.2, 46.4, 59.9, 61.8, 126.6 (2C), 126.8 (2C), 128.4, 128.9 (2C), 129.0, 131.6, 133.5, 136.6, 136.9, 167.9, 171.0, 179.3 and 208.9; HRMS m/z calcd for C24H26N2O5 (M+) 422.18417, found 422.18417. [± The carboxylic acid and amide protons were not observed, presumably, due to rapid exchange with water in the deuteriated NMR solvent.]

Workup

  1. filtrationFiltration of the black Pd residue and evaporation of the filtrate
  2. customgave a pale yellow crude residue
  3. washColumn chromatography on silica gel elution with 37% MeOH-EtOAc

Sources & evidence

ORD record
ord-e714b661c9884c508222d7cfa51cbe2e
Source dataset
uspto-grants-2011_05
Patent number
US07951834B2

Reaction notes

Loading…