HCID 67223158, compound → HCID 67222463, compound

HRID 237311Notes

Reaction equation

HRID 237311 reaction equation
[ClH:1].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:40])[C@H:13]([OH:39])[C@H:14]2[O:19][CH2:18][CH2:17][N:16]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:37])[CH2:28][O:29]CC4C=CC=CC=4)=[CH:22][CH:21]=3)[C:15]2=[O:38])=[CH:7][CH:6]=1)(=[NH:4])[NH2:3]>CO.CC(O)=O.[Pd]>[ClH:1].[C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12](=[O:40])[C@H:13]([OH:39])[C@H:14]2[O:19][CH2:18][CH2:17][N:16]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:37])[CH2:28][OH:29])=[CH:22][CH:21]=3)[C:15]2=[O:38])=[CH:9][CH:10]=1)(=[NH:3])[NH2:4]

Participants

4

Reactant 1

HCID 67223158HCID 67223158, compound

Product 1

HCID 67222463HCID 67222463, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of EXAMPLE 32 (0.12 g) in MeOH—AcOH (20 mL-1 mL), was added 10% Pd—C (20 mg). The reaction mixture was stirred under H2 gas atmosphere at room temperature overnight. The reaction mixture was filtered to remove Pd—C and the filtrate was purified by prep. LC/MS. Before collecting the fractions, conc. HCl was added into each fraction to obtain EXAMPLE 33 (2 mg) as a colorless amorphous solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove Pd—C
  3. customthe filtrate was purified by prep
  4. customBefore collecting the fractions, conc. HCl
  5. additionwas added into each fraction

Sources & evidence

ORD record
ord-d45e30ee5061435ca6dcedb46affac35
Source dataset
uspto-grants-2014_02
Patent number
US08642582B2

Reaction notes

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