HCID 23627853, compound → HCID 23627904, compound

HRID 1423127Notes

Reaction equation

HRID 1423127 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%

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 (30 mg, 0.057 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 the title compound as a colorless foam (14 mg, 56%). LC/MS (Method A) 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-3667ae27dc5a46b1b2d025ac0e82c8bf
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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