Methanol → HCID 49771571, compound

HRID 1173938Notes

Reaction equation

HRID 1173938 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-7d9532ce041e4696a85a8f329109bf76
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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