HCID 23627853, compound → HCID 23627904, compound

HRID 1887217Notes

Reaction equation

HRID 1887217 reaction equation
[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[CH2:28][C:29]([NH:31][O:32]CC1C=CC=CC=1)=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([C@H:8]1[CH2:13][N:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:10][N:9]1[CH2:28][C:29]([NH:31][OH:32])=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 23627853HCID 23627853, compound

Product 1

HCID 23627904HCID 23627904, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-N-benzyloxy-acetamide (Example 71) (30 mg, 0.0566 mmol)was dissolved in MeOH (10 mL), purged with a stream of nitrogen, treated with 20% Pd/C (100 mg, 50% water content), and hydrogenated under 40 psi pressure of hydrogen for 4 h. The crude reaction mixture was then purged with nitrogen, filtered, and evaporated. The crude product was then dissolved in chloroform (5 mL) and filtered through a nylon syringe filter to remove residual Pd/C. The organic solution was evaporated to afford product as a colorless foam (14 mg,. 56%). LC/MS 5.03 min, [M+1]+ 440.

Workup

  1. custompurged with a stream of nitrogen
  2. additiontreated with 20% Pd/C (100 mg, 50% water content)
  3. customThe crude reaction mixture
  4. customwas then purged with nitrogen
  5. filtrationfiltered
  6. customevaporated
  7. dissolutionThe crude product was then dissolved in chloroform (5 mL)
  8. filtrationfiltered through a nylon syringe
  9. filtrationfilter
  10. customto remove residual Pd/C
  11. customThe organic solution was evaporated

Sources & evidence

ORD record
ord-eecfe22ce7c94c8997b6f7abb0fafefc
Source dataset
uspto-grants-2013_08
Patent number
US08501745B2

Reaction notes

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