Dimethyl Sulfide → HCID 86664070, compound

HRID 1424643Notes

Reaction equation

HRID 1424643 reaction equation
[CH2:1]([O:4][C@H:5]1[C@@H:9]([CH2:10][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([N:18]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[N:12]=2)[CH2:8][N:7]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:6]1)[CH:2]=C.[O:40]=[O+][O-].S(C)C>C(Cl)Cl>[C:22]([O:21][C:19]([N:18]([C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[C:13]1[N:12]=[C:11]([CH2:10][C@@H:9]2[C@H:5]([O:4][CH2:1][CH:2]=[O:40])[CH2:6][N:7]([C:33]([O:35][C:36]([CH3:39])([CH3:37])[CH3:38])=[O:34])[CH2:8]2)[CH:16]=[C:15]([CH3:17])[CH:14]=1)=[O:20])([CH3:23])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823Ozone2×HCID 67130096HCID 67130096, compound

Product 1

HCID 86664070HCID 86664070, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5 (100 mg, 0.19 mmol) in CH2Cl2 (10 mL) was cooled to −78° C., to which O3 was charged until the reaction solution turned purple (˜10 min). The O3 flow was stopped, and the reaction was allowed to stir at the same temperature for 30 min. To the resulting solution was added Me2S (150 μL). The reaction mixture was then warmed to room temperature and kept stirring at room temperature for an additional 2 h. The solvent was removed by rotary evaporation and the resulting crude product was purified by flash column chromatography (EtOAc/hexanes, 1:1, Rf=0.2) to yield 6 (87 mg, 87%) as a colorless oil: 1H NMR (500 MHz, CDCl3) δ 1.45 (s, 27H), 2.22 (s, 3H), 2.70-2.85 (m, 111), 2.85-2.95 (m, 1H), 3.05-3.15 (m, 1H), 3.16-3.25 (m, 1H), 3.30-3.37 (m, 1H), 3.45-3.70 (m, 2H), 3.85-3.95 (m, 2H), 4.05-4.20 (t, J=10.0 Hz, 1H), 6.90-6.93 (m, 2H), 9.66 (s, −1H); 13C NMR (125 MHz, CDCl3) δ 20.9, 24.7, 27.9, 28.5, 29.7, 34.4, 42.5, 43.2, 48.8, 49.1, 50.3, 51.0, 74.6, 74.9, 79.4, 79.5, 80.4, 83.0, 119.66, 119.73, 122.8, 149.7, 149.8, 151.57, 151.60, 151.8, 154.4, 154.8, 159.87, 158.94, 200.2, 200.6; LC-TOF (M+H+) calcd for C28H44N3O8 550.3128. found 550.3130.

Workup

  1. additionwas charged until the reaction solution
  2. custom(˜10 min)
  3. stirringkept stirring at room temperature for an additional 2 h
  4. customThe solvent was removed by rotary evaporation
  5. customthe resulting crude product was purified by flash column chromatography (EtOAc/hexanes, 1:1, Rf=0.2)

Sources & evidence

ORD record
ord-81cb0fa2e41940edbd61405a94088842
Source dataset
uspto-grants-2015_01
Patent number
US08927730B2

Reaction notes

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