Dimethyl Sulfoxide → HCID 117761404, compound

HRID 1474650Notes

Reaction equation

HRID 1474650 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:14][C@H:15]1[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@H:18]([C:29]2[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[C:31]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][CH2:45][CH2:46][OH:47])=[CH:40][CH:39]=3)[CH:30]=2)[O:17][C@@H:16]1[CH2:48][O:49][C:50](=[O:52])[CH3:51])(=[O:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.CCCCCC>[C:11]([O:14][C@H:15]1[C@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@@H:19]([O:25][C:26](=[O:28])[CH3:27])[C@H:18]([C:29]2[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[C:31]([CH2:37][C:38]3[CH:39]=[CH:40][C:41]([O:44][CH2:45][CH:46]=[O:47])=[CH:42][CH:43]=3)[CH:30]=2)[O:17][C@@H:16]1[CH2:48][O:49][C:50](=[O:52])[CH3:51])(=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 117761986HCID 117761986, compound

Product 1

HCID 117761404HCID 117761404, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of DMSO (0.04 mL, 0.62 mmol) in dry DCM (1.0 mL) under nitrogen atmosphere, was added oxalyl chloride (0.02 mL, 0.28 mmol) at −78° C. The reaction mixture was stirred at this temperature for 5 min followed by addition of a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-cyano-3-(4-(2-hydroxyethoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (140 mg, 0.24 mmol), in DCM (1 mL). The reaction mixture was stirred at −78° C. for 30 min followed by addition of triethylamine (0.16 mL, 1.20 mmol) and further stirring at same temperature for 10 min and then at r.t. for 10 min. The reaction mixture was diluted with hexane (50 mL) and filtered to remove the solids. The filterate was dried over Na2SO4 and concentrated in vacuo to afford crude title compound (100 mg, 72%) as viscous oil which was used without purification for the next step.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for 30 min
  2. stirringfurther stirring at same temperature for 10 min
  3. waitat r.t. for 10 min
  4. filtrationfiltered
  5. customto remove the solids
  6. dry with materialThe filterate was dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-442d8221a5274b618634b04171ce0659
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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