Dimethyl Sulfide → HCID 117974993, compound

HRID 1776104Notes

Reaction equation

HRID 1776104 reaction equation
[C:1]([O:5][C:6](=[O:34])[N:7]([C@H:11]1[CH2:19][CH2:18][CH2:17][C@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C@@H:15]([O:28][CH2:29][CH:30]=C)[C@H:14]([CH3:32])[O:13][C:12]1=[O:33])[CH2:8][O:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=[O:36].[Na+].O=[O+][O-].CSC>C(Cl)Cl.CO>[C:1]([O:5][C:6](=[O:34])[N:7]([C@H:11]1[CH2:19][CH2:18][CH2:17][C@H:16]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[C@@H:15]([O:28][CH2:29][CH:30]=[O:36])[C@H:14]([CH3:32])[O:13][C:12]1=[O:33])[CH2:8][O:9][CH3:10])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 516892Sodium BicarbonateHCID 117974798HCID 117974798, compound

Product 1

HCID 117974993HCID 117974993, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl((3S,7R,8R,9S)-8-(allyloxy)-7-(4-fluorobenzyl)-9-methyl-2-oxooxonan-3-yl)(methoxymethyl)carbamate (480 mg, 1.001 mmol), NaHCO3 (8.41 mg, 0.10 mmol) and anhydrous MeOH (0.31 mL) in anhydrous CH2Cl2 (9.7 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 then quenched by addition of dimethyl sulfide (0.148 mL, 2.00 mmol). The reaction mixture was warmed to room temperature and stirred for 20 h, concentrated, and purified by column chromatography on SiO2 (gradient, hexanes/EtOAc) to provide the title compound as a mixture of rotamers in the form of a white solid (461 mg, 96%): mp 51-53° C.; IR (neat) 2935, 1740, 1701, 1509, 1367, 1297, 1173, 1081 cm−1; 1H NMR (400 MHz, CDCl3) δ 9.68 (s, 1H), 7.17-7.06 (m, 2H), 7.00-6.91 (m, 2H), 4.99-4.16 (m, 6H), 3.87-2.97 (m, 4H), 2.46-2.27 (m, 1H), 2.17-2.01 (m, 1H), 1.97-1.75 (m, 1H), 1.74-1.37 (m, 17H), 0.95-0.78 (m, 1H); HRMS-ESI (m/z) ([M]+) calcd for C25H36FNO7, 481.2476; found, 481.2481.

Workup

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

Sources & evidence

ORD record
ord-1771c7556dff4f81b2a4287040f0952a
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

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