m-Chloroperbenzoic acid → HCID 58109705, compound

HRID 2037534Notes

Reaction equation

HRID 2037534 reaction equation
[CH2:1]([C@@:4]1([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[CH:15][CH:14]=2)[CH3:12])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:39]>C(Cl)Cl>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[C:16]1[CH:15]=[CH:14][C:13]([C@@H:11]([N:7]2[CH2:6][CH2:5][C@@:4]([C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)([CH2:1][CH:2]3[CH2:3][O:39]3)[O:9][C:8]2=[O:10])[CH3:12])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53472943HCID 53472943, compound

Product 1

HCID 58109705HCID 58109705, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-6-allyl-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (900 mg, 2.0 mmol) in dry CH2Cl2 (30 mL) was added dropwise 3-chlorobenzoperoxoic acid (690 mg, 4.0 mmol) by portion at 0° C. Then the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was quenched by 10% Na2SO3 solution. The organic phase was dried over Na2SO4, filtered and concentrated to afford the residue, which was purified by TLC to give (6S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(oxiran-2-ylmethyl)-1,3-oxazinan-2-one (470 mg, 50%). 1H NMR (CDCl3): 1.54 (m, 3H), 1.71 (m, 3H), 2.01 (m, 1H), 2.15 (m, 3H), 2.48 (m, 2H), 2.67 (m, 1H), 3.00 (m, 1H), 5.67 (m, 1H), 6.84 (m, 4H), 7.02 (m, 2H), 7.21 (m, 4H), 7.31 (m, 1H).

Workup

  1. customThe reaction mixture was quenched by 10% Na2SO3 solution
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford the residue, which
  6. customwas purified by TLC

Sources & evidence

ORD record
ord-4599acf97cc04b72bc73b485c79682bf
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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