HCID 69212799, compound → HCID 67004890, compound

HRID 2187770Notes

Reaction equation

HRID 2187770 reaction equation
ClC1C=CC(C[N:7]2[CH2:11][CH2:10][C@H:9]([NH:12][C:13](=[O:28])[CH2:14][NH:15][C:16](=[O:27])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[CH2:8]2)=CC=1>C(O)=O.CO.[OH-].[OH-].[Pd+2]>[F:26][C:23]([F:24])([F:25])[C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[C:16]([NH:15][CH2:14][C:13]([NH:12][C@H:9]1[CH2:10][CH2:11][NH:7][CH2:8]1)=[O:28])=[O:27]

Participants

4

Reactant 1

HCID 69212799HCID 69212799, compound

Product 1

HCID 67004890HCID 67004890, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 18963719Formic acid methanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of (S)-1-(4-chlorobenzyl)-3-[N-{3(trifluoromethyl)benzoyl}glycyl]aminopyrrolidine (2.93 g, 6.66 mmol) and Pd(OH)2 in 5% HCO2H/methanol (70 mL) was stirred at 60° C. for 3 h. The Pd catalyst was filtered off through Celite, and the filtrate was concentrated. To the residue was added 2 N aqueous NaOH solution (100 mL) and the mixture was extracted with ethyl acetate (100 mL×3). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (SiO2, AcOEt/MeOH/Et3N=85/10/5-60/30/5) gave (S)-3-[N-{3(trifluoromethyl}benzoyl)glycyl]aminopyrrolidine (1.70 g, 81%) as an oil: 1H NMR (CDCl3, 270 MHz) δ 1.76 (d, J=7.3 Hz, 1 H), 2.07-2.25 (m, 1 H), 2.81-2.98 (m, 2 H), 3.02-3.11 (m, 2 H), 4.12 (s, 2 H), 4.41 (br, 1 H), 6.90 (br, 1 H), 7.45 (br, 1 H), 7.58 (dd, J=7.3 and 7.3 Hz, 1 H), 7.77 (d, J =7.3 Hz, 1 H), 8.02 (d, J=7.3 Hz, 1 H), 8.11 (s, 1 H); ESI/MS m/e 316.0 (M++H, C14H16F3N3O2).

Workup

  1. filtrationThe Pd catalyst was filtered off through Celite
  2. concentrationthe filtrate was concentrated
  3. additionTo the residue was added 2 N aqueous NaOH solution (100 mL)
  4. extractionthe mixture was extracted with ethyl acetate (100 mL×3)
  5. washThe combined extracts were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d471e14279ea47de9539e14da7e336f9
Source dataset
uspto-grants-2002_06
Patent number
US06410566B1

Reaction notes

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