HCID 89533746, compound → HCID 117638116, compound

HRID 920264Notes

Reaction equation

HRID 920264 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1/[CH:9]=[CH:10]/[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16]>CO.[Pd]>[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18]

Participants

4

Reactant 1

HCID 89533746HCID 89533746, compound

Product 1

HCID 117638116HCID 117638116, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 33-3 (0.987 g, 3.19 mmol) in MeOH (32 ml) was treated with Pd/C (0.339 g, 0.319 mmol) under an atmosphere of nitrogen in a three-necked round bottomed flask. The vessel was then briefly evacuated, then backfilled with a balloon containing Hydrogen gas. The reaction was stirred at RT for 2 hours, then filtered through celite, washed with MeOH, followed by dichloromethane. Filtrate was concentrated in vacuo and purified by reverse phase chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA) to yield 33-4.

Workup

  1. customThe vessel was then briefly evacuated
  2. additioncontaining Hydrogen gas
  3. filtrationfiltered through celite
  4. washwashed with MeOH
  5. concentrationFiltrate was concentrated in vacuo
  6. custompurified by reverse phase chromatography (C18 column, 5-95% MeCN in water with 0.1% TFA)
  7. customto yield 33-4

Sources & evidence

ORD record
ord-2c2bb9dcb2dd4c24ad284267b56599f0
Source dataset
uspto-grants-2016_03
Patent number
US09273040B2

Reaction notes

Loading…