Methane → HCID 178490235, compound

HRID 530702Notes

Reaction equation

HRID 530702 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH3:46])[CH2:17][N:16]([C:18](=[O:39])[C@H:19]([NH:29][C:30](=[O:38])[CH2:31][CH2:32][C:33]2[N:34]=[CH:35][NH:36][CH:37]=2)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[CH2:15]1)C1C=CC=CC=1.C>C(O)(=O)C.[OH-].[Pd+2].[OH-]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=2[CH3:46])[CH2:15][N:16]([C:18](=[O:39])[C@H:19]([NH:29][C:30](=[O:38])[CH2:31][CH2:32][C:33]2[N:34]=[CH:35][NH:36][CH:37]=2)[CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[CH2:17]1

Participants

5

Reactant 2

HCID 297MethaneHCID 178490236HCID 178490236, compound

Product 1

HCID 178490235HCID 178490235, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

900 mg (1.44 mmol) of N-[(R)-2-[3-(4-benzyloxybutoxy)-3-o-tolylazetidin-1-yl]-1-(4-methoxybenzyl)-2-oxoethyl]-3-(1H-imidazol-4-yl)propionamide are dissolved in 100 ml of acetic acid. 90 mg of 20% palladium hydroxide dispersed on active charcoal are added and the mixture is placed under a dihydrogen atmosphere and stirred for 1 hour at room temperature. The reaction medium is filtered through a layer of Celite and then concentrated to dryness. The crude residue obtained is purified by chromatography on silica gel eluted with an 85/15 dichloromethane/methanol mixture. 440 mg of N-[(R)-2-[3-(4-hydroxybutoxy)-3-o-tolylazetidin-1-yl]-1-(4-methoxybenzyl)-2-oxoethyl]-3-(1H-imidazol-4-yl)propionamide are obtained in the form of a white solid, in a yield of 67%.

Workup

  1. additionare added
  2. filtrationThe reaction medium is filtered through a layer of Celite
  3. concentrationconcentrated to dryness
  4. customThe crude residue obtained
  5. customis purified by chromatography on silica gel
  6. washeluted with an 85/15 dichloromethane/methanol mixture

Sources & evidence

ORD record
ord-26ee61cb8bbf4a39b7d778f7b96d9164
Source dataset
uspto-grants-2016_05
Patent number
US09353083B2

Reaction notes

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