Benzaldehyde dimethyl acetal → HCID 117986152, compound

HRID 1055610Notes

Reaction equation

HRID 1055610 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]23[O:15][C@@:12]([CH2:16][OH:17])([CH2:13][O:14]2)[C@@H:11]([OH:18])[C@H:10]([OH:19])[C@H:9]3[OH:20])=[CH:4][C:3]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH3:30])=[CH:24][CH:23]=1.CO[CH:33](OC)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Na]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]23[O:15][C@@:12]4([CH2:16][O:17][CH:33]([C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)[O:18][C@H:11]4[C@H:10]([OH:19])[C@H:9]2[OH:20])[CH2:13][O:14]3)=[CH:4][C:3]=1[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH3:30])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 62375Benzaldehyde dimethyl acetalHCID 521998p-Toluenesulfonic acid monohydrateHCID 5360545SodiumHCID 44814423Ertugliflozin

Product 1

HCID 117986152HCID 117986152, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol 28a (11.93 g, 27.3 mmol, purchased from Shanghai Caerulum Pharma Discovery Co., Ltd) in acetonitrile (40 mL) were added benzaldehyde dimethyl acetal (12.3 mL, 81.9 mmol) and p-toluenesulfonic acid monohydrate (4.7 g, 27.3 mmol) at room temperature. The mixture was stirred at room temperature for 30 min and adjusted with saturated aqueous sodium bicarnonate till pH becomes 7. The resulting mixture was extracted with ethyl actate (50 mL×2). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=5/1 to give the title compound 28b as a white solid (14.3 g, 100%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl actate (50 mL×2)
  2. washThe combined organic phases were washed with saturated aqueous sodium chloride (30 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified by silica gel chromatography
  7. washeluted with PE/EtOAc(v/v)=5/1

Sources & evidence

ORD record
ord-d5455855e0534f8eab7830cfd5ef841d
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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