HCID 66850357, compound → HCID 66849670, compound

HRID 254346Notes

Reaction equation

HRID 254346 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:33])[NH:22][CH2:23][CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:17][CH:16]=1)C1C=CC=CC=1.[H][H]>[Pd].CO>[C:29]([O:28][C:26](=[O:27])[NH:25][CH2:24][CH2:23][NH:22][C:21](=[O:33])[C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][CH2:12][CH2:11][NH2:10])=[CH:16][CH:17]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

5

Reactant 2

HCID 66850357HCID 66850357, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66849670HCID 66849670, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 32 (0.9 g, 1.92 mmol) with 10% palladium on carbon (0.30 g, wet) in methanol (50 mL) was stirred for 2 h at room temperature under atmospheric pressure of hydrogen. The mixture was then filtered through a silica gel pad. The solvent was evaporated and the residue was purified by Flash™ (BIOTAGE, Inc) (90 g silica gel cartridge 40M, 6:1:0.1 chloroform/ethanol/concentrated ammonium hydroxide) to provide 33 (0.405 g, 63%) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.08 (m, 2H), 1.37 (s, 9H), 1.58 (m, 2H), 2.52 (m, 2H), 3.28 (m, 2H), 6.91 (m, 1H), 7.27 (d, 2H), 7.74 (d, 2H), 8.39 (m, 1H).

Workup

  1. filtrationThe mixture was then filtered through a silica gel pad
  2. customThe solvent was evaporated
  3. customthe residue was purified by Flash™ (BIOTAGE, Inc) (90 g silica gel cartridge 40M, 6:1:0.1 chloroform/ethanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-e290b9b709b34d3d975f87ed52c45f1c
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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