Methanol → HCID 59235335, compound

HRID 2174336Notes

Reaction equation

HRID 2174336 reaction equation
[Cl:1][C:2]1[C:3]([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([CH2:57][CH3:58])=[CH:53][CH:52]=2)=[CH:4][C:5]([C@H:11]2[C@H:16]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@@H:15]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:14]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@@H:13]([CH2:41][O:42][CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[O:12]2)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O.[CH3:63]O>>[Cl:1][C:2]1[C:3]([CH2:50][C:51]2[CH:52]=[CH:53][C:54]([CH2:57][CH3:58])=[CH:55][CH:56]=2)=[CH:4][C:5]([C@H:11]2[C@H:16]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C@@H:15]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@H:14]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@@H:13]([CH2:41][O:42][CH2:43][C:44]3[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[O:12]2)=[C:6]([CH:10]=1)[C:7]([O:9][CH3:63])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 59235333HCID 59235333, compound

Product 1

HCID 59235335HCID 59235335, compound

Procedure

To a cold (0° C.) stirred solution of 5-chloro-4-(4-ethylbenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzoic acid (0.15 g, 0.188 mmol) in methanol (10 mL) was added dropwise sulfurous dichloride (0.034 g, 0.021 mL). The mixture was heated to reflux and kept refluxing overnight. The volatiles were removed under reduced pressure, and the residue was quenched with water. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed with saturated sodium bicarbonate, then with water and then with brine, and dried over anhydrous sodium sulfate. After removal of the volatiles, 153 mg of crude solid product was obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperaturekept refluxing overnight
  4. customThe volatiles were removed under reduced pressure
  5. customthe residue was quenched with water
  6. customThe organic phase was separated
  7. extractionthe aqueous phase was extracted with ethyl acetate
  8. washwashed with saturated sodium bicarbonate
  9. dry with materialwith water and then with brine, and dried over anhydrous sodium sulfate
  10. customAfter removal of the volatiles

Sources & evidence

ORD record
ord-3df4c4dab43a453ebbaf2b41d3b60e3c
Source dataset
uspto-grants-2015_06
Patent number
US09061060B2

Reaction notes

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