HCID 54100165, compound → HCID 22956155, compound

HRID 2120164Notes

Reaction equation

HRID 2120164 reaction equation
[CH2:1]([O:3][C:4](=[O:41])[CH:5]([NH:22][C:23]([C:25]1([NH:30][C:31](=[O:40])[CH:32]([S:36][C:37](=[O:39])[CH3:38])[CH:33]([CH3:35])[CH3:34])[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)=[CH:11][CH:12]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:41])[CH:5]([NH:22][C:23]([C:25]1([NH:30][C:31](=[O:40])[CH:32]([S:36][C:37](=[O:39])[CH3:38])[CH:33]([CH3:35])[CH3:34])[CH2:26][CH2:27][CH2:28][CH2:29]1)=[O:24])[CH2:6][C:7]1[CH:8]=[N:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 54100165HCID 54100165, compound

Product 1

HCID 22956155HCID 22956155, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 2-{[1-(2-acetylthio-3-methyl-butanoylamino)-cyclopentanecarbonyl]-amino}-3-[6-(3-nitro-phenyl)-pyridin-3-yl]-propanoic acid ethyl ester (110 mg) and 25 mg of 10% Pd/C in 10 mL of EtOH is stirred under a H2 atmosphere for 18 h. The catalyst is filtered off, and the reaction mixture is concentrated in vacuo. The residue is purified by chromatography on silica gel (50% EtOAc/hexane) to produce yellow product; 1H NMR (250 MHz, CDCl3) δ8.39 (d, 1H), 7.60 (s, 2H), 7.10-7.36 (m, 3H), 6.71 (d, 1H), 6.34 (d, 1H), 4.76 (app q, 1H), 4.15 (q, 2H), 3.62 (dd, 1H), 3.05-3.25 (m, 2H), 2.35, 2.32 (two s, 3H), 1.55-2.40 (m, 9H), 1.19 (t, 3H), 0.92-1.06 (m, 6H).

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe reaction mixture is concentrated in vacuo
  3. customThe residue is purified by chromatography on silica gel (50% EtOAc/hexane)
  4. customto produce yellow product

Sources & evidence

ORD record
ord-41ffc7ee9cf6470482c03ec380dff4d2
Source dataset
uspto-grants-2004_02
Patent number
US06689801B2

Reaction notes

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