p-Toluenesulfonic acid monohydrate → HCID 67153941, compound

HRID 1055500Notes

Reaction equation

HRID 1055500 reaction equation
C([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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:36]([Cl:39])=[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)([O:31]C)[O:11][C:10]1([CH2:52]O)[CH2:50][OH:51])C1C=CC=CC=1.O.[C:55]1([CH3:65])[CH:60]=[CH:59][C:58](S(O)(=O)=O)=[CH:57][CH:56]=1>ClCCl>[CH2:65]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=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:36]([Cl:39])=[C:35]([CH2:40][C:41]4[CH:46]=[CH:45][C:44]([O:47][CH2:48][CH3:49])=[CH:43][CH:42]=4)[CH:34]=3)[O:11][C@@:10]1([CH2:50][OH:51])[CH2:52][O:31]2)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 91828158HCID 91828158, compound

Product 1

HCID 67153941HCID 67153941, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol 1i (2.49 g, 3.37 mmol) in dichloromethane (300 mL) was added p-toluenesulfonic acid monohydrate (0.32 g, 1.69 mmol) at room temperature. The mixture was stirred at room temperature for 1 hour and quenched with 30 mL of saturated aqueous sodium bicarbonate. The resulting mixture was extracted with dichloromethane (20 mL×2). The combined organic layers were washed with saturated aqueous sodium chloride (20 mL×2), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=7/1 to give the title compound 1j as pale yellow oil (1.06 g, 44.5%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ (ppm): 7.45 (d, 1H), 7.40 (m, 12H), 7.30 (m, 3H), 7.09 (m, 2H), 6.91 (m, 2H), 6.78 (m, 2H), 4.88 (m, 3H), 4.78 (d, 1H), 4.29 (m, 2H), 4.11-3.96 (m, 6H), 3.88 (d, 1H), 3.80 (m, 2H), 3.71 (m, 2H), 1.85 (t, 1H), 1.41 (t, 3H).

Workup

  1. customquenched with 30 mL of saturated aqueous sodium bicarbonate
  2. extractionThe resulting mixture was extracted with dichloromethane (20 mL×2)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride (20 mL×2)
  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)=7/1

Sources & evidence

ORD record
ord-27e0be887cfe4b099e883e8134ed1fbe
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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