m-Chloroperbenzoic acid → HCID 66857511, compound

HRID 1046135Notes

Reaction equation

HRID 1046135 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH2:29][CH2:30][C:31](N)=[O:32])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:42])C=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([CH2:29][CH2:30][C:31]([OH:32])=[O:42])[O:13][C:12](=[O:14])[N:11]([C@H:15]([C:17]3[CH:22]=[CH:21][C:20]([C:23]4[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=4)=[CH:19][CH:18]=3)[CH3:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 58109411HCID 58109411, compound

Product 1

HCID 66857511HCID 66857511, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-((R)-6-(4-fluorophenyl)-2-oxo-3-((S)-1-(4-(pyridin-3-yl)phenyl)ethyl)-1,3-oxazinan-6-yl) propanamide (70 mg, 0.16 mmol) in CH2Cl2 (10 mL), was added m-CPBA (135 mg, 0.79 mmol), and the reaction mixture was stirred at rt for 3 h. After the solvent was removed under reduced pressure, the residue was purified by preparative TLC to afford 3-((R)-6-(4-fluorophenyl)-2-oxo-3-((S)-1-(4-(pyridin-3-yl)phenyl)ethyl)-1,3-oxazinan-6-yl)propanoic acid (10 mg, 15%). LC-MS Method 2 tR=0.987 min, m/z=464.17; 1H NMR (CDCl3): 1.51 (m, 3H), 1.92 (m, 1H), 2.12-2.28 (m, 5H), 2.43 (m, 1H), 2.95 (m, 1H), 5.56 (m, 1H), 5.65 (m, 1H), 5.31 (m, 1H), 6.95 (m, 2H), 7.08 (m, 2H), 7.15 (m, 1H), 7.20 (m, 1H), 7.25 (m, 2H), 7.56 (m, 1H), 7.24 (m, 1H), 8.35 (m, 1H), 8.65 (m, 1H).

Workup

  1. customAfter the solvent was removed under reduced pressure
  2. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-93fa3693501b401ca3dea7e98ec4d057
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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