Ozone → HCID 58109636, compound

HRID 2037536Notes

Reaction equation

HRID 2037536 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][C@@:7]1([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[O:12][C:11](=[O:13])[N:10]([C@H:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=3[F:29])=[CH:18][CH:17]=2)[CH3:15])[CH2:9][CH2:8]1)[CH:2]=C.[O:37]=[O+][O-].[BH4-].[Na+]>C(Cl)Cl>[F:29][C:23]1[CH:24]=[C:25]([F:28])[CH:26]=[CH:27][C:22]=1[C:19]1[CH:20]=[CH:21][C:16]([C@@H:14]([N:10]2[CH2:9][CH2:8][C@@:7]([C:30]3[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=3)([CH2:6][CH2:5][O:4][CH2:1][CH2:2][OH:37])[O:12][C:11]2=[O:13])[CH3:15])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 24823OzoneHCID 4311764Sodium borohydrideHCID 58109363HCID 58109363, compound

Product 1

HCID 58109636HCID 58109636, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (S)-6-(2-(allyloxy)ethyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (100 mg, 0.20 mmol) in CH2Cl2 (10 mL) was treated with O3 at −78° C. till the mixture was turned blue. Then NaBH4 (50 mg, 1.0 mmol) was added, and the mixture was stirred at rt overnight. The solution was concentrated and the residue was purified by preparative HPLC to give (S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-(2-hydroxyethoxy)ethyl)-1,3-oxazinan-2-one (40 mg, 30%). LC-MS Method 3 tR=1.41, min, m/z=500, 522; 1H NMR (CDCl3): 1.48-1.61 (d, 3H), 1.92-2.05 (m, 2H), 2.09-2.41 (m, 5H), 2.88-3.02 (m, 1H), 3.27-3.56 (m, 2H), 3.58-3.69 (m, 2H), 5.63-5.72 (m, 1H), 6.82-7.08 (m, 6H), 7.17-7.34 (m, 5H).

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-80312b9c0b79414da44174671b7be0ac
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

Loading…