HCID 57956925, compound → HCID 11992492, compound

HRID 553073Notes

Reaction equation

HRID 553073 reaction equation
C([O:8][C:9](=[O:37])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:36])[CH2:16][CH2:17][C:18](=[O:35])[C@@H:19]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[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:21]1([CH2:20][C@H:19]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:18](=[O:35])[CH2:17][CH2:16][C:15]([N:11]2[CH2:12][CH2:13][CH2:14][C@H:10]2[C:9]([OH:37])=[O:8])=[O:36])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 57956925HCID 57956925, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11992492HCID 11992492, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a stirred solution of the benzyl ester 10 (100 mg, 0.1968 mmol) in dry EtOAc-MeOH (3:1 ratio) (10 mL) was added 10% Pd/C (50 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 crude residue. Column chromatography on silica gel elution with 20% MeOH-EtOAc afforded (5S)-6-phenyl-5-[(tert-butyloxycarbonyl)-amino]-4-oxo-hexanoyl-L-proline 11a as a pale colourless oil (74 mg, 90%); Rf 0.23 (20% MeOH-EtOAc); IR (liquid film) ν 1720 (CO), 3000 (broad, COOH) cm−1; 1H NMR (300 MHz, CDCl3) δH 1.39 (9H, s, (CH3)3), 2.04 (2H, m, —CH2—), 2.44 (1H, br-s, —COOH), 2.62 (4H, m,), 2.94 (3H, m), 3.16 (1H, m), 3.60 (2H, m, —CH2N—), 4.52 (2H, m, 2×—CH—), 5.08 (1H, m, —NH—) and 7.14-7.35 (5H, m, Ar—H); 13C NMR (75 MHz, CDCl3) δC 21.0, 22.6, 24.7, 28.0, 29.2, 30.9, 31.4, 34.6, 46.9, 58.7, 60.4, 126.8, 127.0, 128.5, 128.7, 129.5, 136.4, 155.3, 171.8, 173.7, 207.5 and 208.0; HRMS m/z calcd for C22H30N2O6 (M+) 418.21734, found 418.21039.

Workup

  1. filtrationFiltration of the black Pd residue and evaporation of the filtrate
  2. customgave a crude residue
  3. washColumn chromatography on silica gel elution with 20% MeOH-EtOAc

Sources & evidence

ORD record
ord-284f535c61434f0bade0ebba48eac4af
Source dataset
uspto-grants-2011_05
Patent number
US07951834B2

Reaction notes

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