Dimethyl Sulfoxide → HCID 89442768, compound

HRID 1474606Notes

Reaction equation

HRID 1474606 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=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]([Cl:35])=[C:31]([CH2:36][C:37]3[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH2:45][OH:46])=[CH:39][CH:38]=3)[CH:30]=2)[O:17][C@@H:16]1[CH2:47][O:48][C:49](=[O:51])[CH3:50])(=[O:13])[CH3:12].CCN(CC)CC>C(Cl)Cl>[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]([Cl:35])=[C:31]([CH2:36][C:37]3[CH:38]=[CH:39][C:40]([O:43][CH2:44][CH:45]=[O:46])=[CH:41][CH:42]=3)[CH:30]=2)[O:17][C@@H:16]1[CH2:47][O:48][C:49](=[O:51])[CH3:50])(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 89442952HCID 89442952, compound

Product 1

HCID 89442768HCID 89442768, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.042 mL, 0.51 mmol) was added to a solution of DMSO (0.071 mL, 1.01 mmol) in dry DCM (0.5 mL) at −78° C. under nitrogen atmosphere. The reaction mixture was stirred for 5 min. at the same temperature and then a solution of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(2-hydroxyethoxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (150 mg, 0.25 mmol), in dry DCM (2 mL) was added. The reaction mixture was stirred at the same temperature for 1 h. NEt3 (0.211 mL, 1.518 mmol) was added and the reaction mixture was allowed to come to r.t. The crude compound was extracted with DCM (20 mL). The organic layer was separated, washed with water (15 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to afford the title compound which was used as such in next step.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 1 h
  2. customto come to r.t
  3. extractionThe crude compound was extracted with DCM (20 mL)
  4. customThe organic layer was separated
  5. washwashed with water (15 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7dde43bbd180457b9b3e7c118546e8eb
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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