Dimethyl Sulfoxide → HCID 89442841, compound

HRID 1474614Notes

Reaction equation

HRID 1474614 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]([O:29][CH3:30])[O:17][C@H:16]1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH2:47][OH:48])=[CH:41][CH:40]=2)[CH:32]=1)(=[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]([O:29][CH3:30])[O:17][C@H:16]1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([CH2:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][CH2:46][CH:47]=[O:48])=[CH:41][CH:40]=2)[CH:32]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 117762492HCID 117762492, compound

Product 1

HCID 89442841HCID 89442841, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.068 mL, 0.80 mmol) was added to a solution of DMSO (0.113 mL, 1.60 mmol) in dry DCM (1 mL) at −78° C. under nitrogen atmosphere. The reaction mixture was stirred for 5 min. at the same temperature and then a solution of (2S,3S,4R,5S,6S)-2-(4-chloro-3-(4-(2-hydroxyethoxy)benzyl)phenyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (220 mg, 0.403 mmol), in dry DCM (3 mL) was added. The reaction mixture was stirred at the same temperature for 1 h. NEt3 (0.334 mL, 2.40 mmol) was added and the reaction mixture was allowed to come to r.t. The crude compound was extracted with DCM (30 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 (30 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-27386d14573344f6ae3dd08dc0f75881
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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