Methanol → HCID 49771571, compound

HRID 348686Notes

Reaction equation

HRID 348686 reaction equation
C(OC(=O)[N:10]([CH:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH2:42]1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]([CH2:35][C:36]3[NH:37][CH:38]=[CH:39][N:40]=3)[CH2:28][C:29]3[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=3)=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)C1C=CC=CC=1.[H][H].C[OH:51]>C(O)C.[C].[Pd]>[CH:41]1([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:51])[C:20]3[CH:21]=[CH:22][C:23]([CH2:26][N:27]([CH2:35][C:36]4[NH:40][CH:39]=[CH:38][N:37]=4)[CH2:28][C:29]4[N:30]([CH3:34])[CH:31]=[CH:32][N:33]=4)=[CH:24][CH:25]=3)=[CH:16][CH:17]=2)[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]1

Participants

6

Reactant 3

HCID 887MethanolHCID 66941754HCID 66941754, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 49771571HCID 49771571, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

The compound (212 mg) obtained in Example 87-5 was dissolved in methanol (10 ml). After having been cooled with ice, the solution was added with a suspension of 10% palladium-carbon (105 mg) in ethanol (3.0 ml). After having been subjected to hydrogen displacement, the mixture was stirred under a hydrogen atmosphere at room temperature for 3 hours. After the reaction, the solution was filtrated through Celite and the solvent was then distilled off. Then, the residue was purified through silica gel column chromatography (chloroform/methanol) and treated with hydrochloric acid, thereby obtaining hydrochloride (43.1 mg) of the subject compound as a white solid.

Workup

  1. temperatureAfter having been cooled with ice
  2. customAfter the reaction
  3. filtrationthe solution was filtrated through Celite
  4. distillationthe solvent was then distilled off
  5. customThen, the residue was purified through silica gel column chromatography (chloroform/methanol)
  6. additiontreated with hydrochloric acid

Sources & evidence

ORD record
ord-c78bc65b881f477a8b50c4a0f7d59f98
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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