HCID 68752619, compound → 2-(1-(3-Tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid

HRID 333296Notes

Reaction equation

HRID 333296 reaction equation
C([O:8][C:9](=[O:37])[CH2:10][C:11]1([C:16]([NH:18][CH2:19][CH:20]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=2)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1)C1C=CC=CC=1>CCO.[Pd]>[C:24]([O:23][C:21](=[O:22])[CH:20]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=1)[CH2:19][NH:18][C:16]([C:11]1([CH2:10][C:9]([OH:37])=[O:8])[CH2:12][CH2:13][CH2:14][CH2:15]1)=[O:17])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 1

HCID 68752619HCID 68752619, compound

Product 1

HCID 687477812-(1-(3-Tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acidYield 45.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of tert-butyl 3-(1-(2-(benzyloxy)-2-oxoethyl)cyclopentanecarboxamido)-2-(3,4-dichlorobenzyl)propanoate (81.2 mg, 0.148 mmol) and Pd/C (31.5 mg, 0.015 mmol) in EtOH (1 ml) was allowed to stir under hydrogen atmosphere (1 atm) for 6.5 hr. The reaction mixture was filtered, and the filter cake was washed with MeOH. The combined filtrate was concentrated under reduced pressure. The obtained residue was purified by RP-HPLC (X-Bridge C18, H2O (0.1% NH4OH)/CH3CN) to give 2-(1-(3-tert-butoxy-2-(3,4-dichlorobenzyl)-3-oxopropylcarbamoyl)cyclopentyl)acetic acid (30.6 mg); Retention time=1.30 minutes (condition B); MS (m+1)=458.2; 1H NMR (400 MHz, CDCl3, data for major rotamer) δ ppm 1.37 (s, 9H) 1.70-1.98 (m, 8H) 2.64-2.88 (m, 5H) 3.34-3.53 (m, 2H) 6.53-6.56 (m, 1H) 7.02-7.04 (m, 1H) 7.28 (d, J=2.0 Hz, 1H) 7.36 (d, J=8.0 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake was washed with MeOH
  3. concentrationThe combined filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified by RP-HPLC (X-Bridge C18, H2O (0.1% NH4OH)/CH3CN)

Sources & evidence

ORD record
ord-7a378b70347343958732246d0b67a657
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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