4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[1-(3-butenyl)cyclopentyl]carbonyl]-L-phenylalanine methyl ester → HCID 53679876, compound

HRID 393462Notes

Reaction equation

HRID 393462 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=2[Cl:34])=[O:26])=[CH:20][CH:19]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][CH:15]=[CH2:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7]>[Pd].CCO>[CH3:1][O:2][C:3](=[O:35])[C@H:4]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:25]([C:27]2[C:28]([Cl:34])=[CH:29][CH:30]=[CH:31][C:32]=2[Cl:33])=[O:26])=[CH:22][CH:23]=1)[NH:5][C:6]([C:8]1([CH2:13][CH2:14][CH2:15][CH3:16])[CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7]

Participants

4

Reactant 1

HCID 545023014-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[1-(3-butenyl)cyclopentyl]carbonyl]-L-phenylalanine methyl ester

Product 1

HCID 53679876HCID 53679876, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-[[(2,6-dichlorophenyl)carbonyl]amino]-N-[[1-(3-butenyl)cyclopentyl]carbonyl]-L-phenylalanine methyl ester (0.19 mmol, 100 mg) and 10% palladium on carbon (200 mg) in EtOH (2 mL) was stirred under a hydrogen atmosphere at room temperature for 15 h. Then, the charcoal was filtered and washed with EtOH (10 mL). The filtrate was removed under vacuum to obtain 37.5 mg (37%) of as a white solid: mp 193-196° C. HR MS: Obs. mass, 519.1818. Calcd. mass, 519.1817 (M+H).

Workup

  1. filtrationThen, the charcoal was filtered
  2. washwashed with EtOH (10 mL)
  3. customThe filtrate was removed under vacuum
  4. customto obtain 37.5 mg (37%) of as a white solid

Sources & evidence

ORD record
ord-6ac51f36ae334cfb848d016c25071ca1
Source dataset
uspto-grants-2004_10
Patent number
US06806365B2

Reaction notes

Loading…