Potassium Carbonate → (1S,2R,3S,4R,5S)-3,4-dibenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-2-ol

HRID 1055618Notes

Reaction equation

HRID 1055618 reaction equation
C([O:4][CH2:5][C@:6]12[O:13][C@:10]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([CH2:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[CH:24][CH:23]=4)[CH:15]=3)([O:11][CH2:12]1)[C@H:9]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C@@H:8]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C@H:7]2[OH:47])(=O)C.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CO>[CH2:40]([O:39][C@@H:8]1[C@@H:9]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C@:10]2([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([CH2:21][C:22]4[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH3:30])=[CH:26][CH:27]=4)[CH:15]=3)[O:13][C@@:6]([CH2:5][OH:4])([CH2:12][O:11]2)[C@@H:7]1[OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 122610451[(1R,2R,3S,4R,5S)-3,4-dibenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-1-yl]methyl acetate

Product 1

HCID 118391255(1S,2R,3S,4R,5S)-3,4-dibenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-2-olYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [(1R,2R,3S,4R,5S)-3,4-dibenzyloxy-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-1-yl]methyl acetate 28i (237 mg, 0.36 mmol) in methanol (20 mL) was added potassium carbonate (199 mg, 1.44 mmol) at room temperature. The mixture was stirred at room temperature for 5 min and adjusted with saturated aqueous ammonium chloride till pH becomes 7. The resulting mixture was extracted with ethyl acetate (10 mL×3). The combined organic layers were washed with saturated aqueous sodium chloride (10 mL×3), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 28j as a white solid (222 mg, 100%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (10 mL×3)
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride (10 mL×3)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-15535623bd1c444683dac3bcb3bb1eda
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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