Dimethyl Sulfide → HCID 86701329, compound

HRID 1627053Notes

Reaction equation

HRID 1627053 reaction equation
[CH2:1]([O:4][C@H:5]1[C@H:13]([CH3:14])[O:12][C:11](=[O:15])[C@@H:10]([N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:9][O:8][CH2:7][C@@H:6]1[O:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH:2]=C.C([O-])(O)=[O:37].[Na+].O=[O+][O-].CSC>CO.C(Cl)Cl>[C:19]([O:18][C:17]([N:16]([C@H:10]1[CH2:9][O:8][CH2:7][C@H:6]([O:31][CH2:32][CH2:33][CH2:34][CH3:35])[C@@H:5]([O:4][CH2:1][CH:2]=[O:37])[C@H:13]([CH3:14])[O:12][C:11]1=[O:15])[C:24](=[O:25])[O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:23])([CH3:21])([CH3:22])[CH3:20]

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 516892Sodium BicarbonateHCID 86701330HCID 86701330, compound

Product 1

HCID 86701329HCID 86701329, compoundYield 907.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl N-[(3S,7S,8S,9S)-8-allyloxy-7-butoxy-9-methyl-2-oxo-1,5-dioxonan-3-yl]-N-tert-butoxycarbonylcarbamate (0.350 g, 0.698 mmol) and NaHCO3 (5.86 mg, 0.070 mmol) in MeOH (0.21 ml) and DCM (6.8 ml) was treated with ozone at −78° C. until the solution became light blue in color. The mixture was purged with nitrogen until colorless and quenched by the addition of DMS (0.10 ml, 1.40 mmol). The reaction mixture was slowly warmed to room temperature and stirred for 20 h. The mixture was concentrated and purified by flash chromatography on (SiO2, hexanes/EtOAc gradient) to yield the title compound as a colorless oil (320 mg, 91%): IR (neat) 2934, 2876, 1743, 1706, 1367, 1253, 1121, 1096 cm−1; 1H NMR (400 MHz, CDCl3) δ 9.63 (s, 1H), 5.18 (dd, J=8.9, 3.8 Hz, 1H), 4.84 (dq, J=9.4, 6.3 Hz, 1H), 4.39 (dd, J=17.9, 0.9 Hz, 1H), 4.22 (dd, J=17.8, 0.5 Hz, 1H), 4.19 (dd, J=12.2, 3.8 Hz, 1H), 3.91-3.75 (m, 2H), 3.57-3.42 (m, 2H), 3.37 (dt, J=9.2, 6.5 Hz, 1H), 3.29 (dd, J=7.9, 6.9 Hz, 1H), 3.21 (t, J=9.0 Hz, 1H), 1.52-1.40 (m, 2H), 1.45 (s, 18H), 1.41 (d, J=6.3 Hz, 3H), 1.30-1.19 (m, 2H), 0.83 (t, J=7.3 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 200.51, 168.79, 152.61, 86.19, 83.52, 83.08, 79.09, 75.35, 72.95, 71.99, 70.03, 57.92, 32.02, 27.94, 19.29, 18.84, 13.85; HRMS-ESI (m/z) [M]+ calcd for C24H41NO10, 503.2730; found, 503.2727.

Workup

  1. customThe mixture was purged with nitrogen until colorless and
  2. concentrationThe mixture was concentrated
  3. custompurified by flash chromatography on (SiO2, hexanes/EtOAc gradient)

Sources & evidence

ORD record
ord-66533837163c41e8af0cf8018f27e04c
Source dataset
uspto-grants-2014_07
Patent number
US08785479B2

Reaction notes

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