HCID 57796841, compound → HCID 57495455, compound

HRID 1362582Notes

Reaction equation

HRID 1362582 reaction equation
C([O:8][NH:9][C:10](=[O:45])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:44])[C@@H:18]([NH:29][C:30](=[O:43])[CH2:31][CH2:32][CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][NH:9][C:10](=[O:45])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:44])[C@@H:18]([NH:29][C:30](=[O:43])[CH2:31][CH2:32][CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)[CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1

Participants

4

Reactant 1

HCID 57796841HCID 57796841, compound

Product 1

HCID 57495455HCID 57495455, compoundYield 410.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(Method J15F) 6-[3-(1H-Indol-3-yl)-2-(4-1H-indol-3-yl-butyrylamino)-propionylamino]-hexanoic acid benzyloxy-amide (19/97) (1.654 g, 0.274 mmol) was dissolved in ethanol (20 ml), 10% Pd/C (50 mg) was added and the reaction mixture was hydrogenated at room temperature for 4 hours. The catalyst was filtered off, the solvent was evaporated and the residue was chromatographed on silica gel with acetonitrile-acetic acid (60:1) and acetonitrile-acetic acid-water (30:1:1) as eluent to give the title product (0.582 g, 41%) as white powder. M.p. 94-96° C. 1H NMR (DMSO-d6, HMDSO), δ: 1.06-1.55 (m, 6H); 1.68-1.97 (m, 4H); 2.04-2.27 (m, 2H); 2.42-2.67 (m, 2H overlapped with DMSO) 2.80-3.15 (m, 4H); 4.44-4.57 (m, 1H); 6.87-7.17 (m, 6H); 7.31 (d, 2H, J=7.6 Hz); 7.44 (d, 1H, J=7.6 Hz); 7.58 (d, 1H, J=7.6 Hz); 7.80-8.03 (m, 2H); 8.67 (s, 1H); 10.33 (s, 1H); 10.72 (s, 1H); 10.76 ppm (s, 1H). HPLC analysis on Symmetry C8 column: impurities 2.5% (column size 3.9×150 mm; mobile phase acetonitrile −0.1 M phosphate buffer (pH 2.5), 35:65; detector UV 220 nm; sample concentration 0.5 mg/ml, flow rate 1.0 ml/min). Anal. Calcd for C29H35N5O4: C, 67.29; H, 6.82; N, 13.53. Found: C, 67.06; H, 6.86; N, 13.66.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated
  3. customthe residue was chromatographed on silica gel with acetonitrile-acetic acid (60:1) and acetonitrile-acetic acid-water (30:1:1) as eluent

Sources & evidence

ORD record
ord-bab4e3b228f747b893646a4266452ebc
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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