HCID 86591374, compound → HCID 21882818, compound

HRID 722138Notes

Reaction equation

HRID 722138 reaction equation
[F:1][C:2]1[C:3]2[CH2:4][CH:5]3[C:14](=[N:15]O)[CH:8]([CH2:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)[CH2:7][CH2:6]3>CC(O)=O.[OH-].[Na+].[Pt](=O)=O>[F:1][C:2]1[C:3]2[CH2:4][CH:5]3[CH:14]([NH2:15])[CH:8]([CH2:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)[CH2:7][CH2:6]3

Participants

5

Reactant 1

HCID 86591374HCID 86591374, compound

Product 1

HCID 21882818HCID 21882818, compoundYield 95.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

The oxime from Step 3 (590 mg, 2.69 mmol) and platinum dioxide (40 mg) in AcOH (20 ml) were hydrogenated in a Parr reactor at 30 psi for 2 hours. The mixture was filtered through Celite and the filtrate was concentrated by lyophilization to give an off-white solid. The solid was dispersed in 1N NaOH and extracted with DCM. The organic extract was dried and concentrated to dryness to give a yellow oil 525 mg (95%). m/z 206 (M+H+).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated by lyophilization
  3. customto give an off-white solid
  4. extractionextracted with DCM
  5. extractionThe organic extract
  6. customwas dried
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f105cd18c83d4c0a84a55a9258d0b196
Source dataset
uspto-grants-2006_11
Patent number
US07138400B2

Reaction notes

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