m-Chloroperbenzoic acid → HCID 178520769, compound

HRID 1396977Notes

Reaction equation

HRID 1396977 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:25][C:26](=[O:36])[NH:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=3)=[O:16])[CH2:13][CH:12]=[N:11]2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=C(C(OO)=[O:45])C=CC=1>ClCCl>[CH:1]1([CH2:6][C@H:7]([CH2:25][C:26](=[O:36])[NH:27][O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N+:19]=3[O-:45])=[O:16])[CH2:13][CH:12]=[N:11]2)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86706398(5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide

Product 1

HCID 178520769HCID 178520769, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of (5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(5-fluoro-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (140 mg, 0.28 mmol) in dichloromethane (DCM) (5 mL) under nitrogen at 0° C. was added 3-chlorobenzenecarboperoxoic acid (147 mg, 0.85 mmol) in one portion. The reaction mixture was stirred at 0° C. for 10 min, then warmed to room temperature and stirred overnight. The reaction mixture was quenched with sat. aq. NaHCO3 and then extracted with DCM. The organics were dried over Na2SO4, filtered, and concentrated to provide the crude product which was purified by Gilson HPLC (Sunfire Column 19×50 mm, flowrate 25 mL/min, 10 min, 5-65% MeCN:H2O) to afford (5S)-1-((2R)-2-(cyclopentylmethyl)-4-oxo-4-{[(phenylmethyl)oxy]amino}butanoyl)-N-(5-fluoro-1-oxido-2-pyridinyl)-4,5-dihydro-1H-pyrazole-5-carboxamide (90 mg, 0.18 mmol, 62% yield) as a white solid. MS: 512 ([M]+).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred overnight
  3. customThe reaction mixture was quenched with sat. aq. NaHCO3
  4. extractionextracted with DCM
  5. dry with materialThe organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto provide the crude product which
  9. customwas purified by Gilson HPLC (Sunfire Column 19×50 mm, flowrate 25 mL/min, 10 min, 5-65% MeCN:H2O)

Sources & evidence

ORD record
ord-cd3faa759781448abb14e7415defecc1
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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