Dichloromethane → HCID 117928698, compound

HRID 1055519Notes

Reaction equation

HRID 1055519 reaction equation
C(O[C@H:9]1[C@H:14](OCC2C=CC=CC=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@:12]([C:33]2[CH:38]=[CH:37]C(Cl)=[C:35]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[CH:43][CH:42]=3)[CH:34]=2)(OC)[O:11][C@:10]1([C:52]([OH:55])([CH3:54])[CH3:53])[CH2:50][OH:51])C1C=CC=CC=1.[OH2:56].[C:57]1([CH3:67])[CH:62]=[CH:61][C:60](S(O)(=O)=O)=[CH:59][CH:58]=1.Cl[CH2:69][Cl:70]>>[CH2:67]([O:56][C@H:9]1[C@H:14]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@:12]2([C:33]3[CH:38]=[CH:37][C:69]([Cl:70])=[C:35]([CH2:40][C:41]4[CH:42]=[CH:43][C:44]([O:47][CH2:48][CH3:49])=[CH:45][CH:46]=4)[CH:34]=3)[O:11][C@@:10]1([CH2:50][OH:51])[C:52]([CH3:53])([CH3:54])[O:55]2)[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 117928876HCID 117928876, compound

Product 1

HCID 117928698HCID 117928698, compoundYield 28%

Procedure

To a solution of 2-[(2R,3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]propan-2-ol 9c (0.23 g, 0.30 mmol) in dichloromethane (60 mL) was added p-toluenesulfonic acid monohydrate (25.30 mg, 0.13 mmol) at room temperature. The mixture was stirred at room temperature for 21 hours and quenched with 15 mL of saturated aqueous sodium bicarbonate. The mixture was partitioned. The organic layer was washed with saturated aqueous sodium chloride (15 mL×3), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=10/1 to give the title compound 9d as colorless oil (50.00 mg, 28%).

Workup

  1. customquenched with 15 mL of saturated aqueous sodium bicarbonate
  2. customThe mixture was partitioned
  3. washThe organic layer was washed with saturated aqueous sodium chloride (15 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluted with PE/EtOAc(v/v)=10/1

Sources & evidence

ORD record
ord-662a901c6d1949a0a6c487574115379d
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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