Trifluoroacetic acid → HCID 86729344, compound

HRID 1474599Notes

Reaction equation

HRID 1474599 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2(OC)[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C:10]([CH2:19][OH:20])([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]23[O:9][C@@:10]([CH2:19][OH:20])([CH2:17][O:18]2)[C@@H:11]([OH:16])[C@H:12]([OH:15])[C@H:13]3[OH:14])=[CH:4][C:3]=1[CH2:23][O:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86729343HCID 86729343, compound

Product 1

HCID 86729344HCID 86729344, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,3R,4S,5S)-2-(4-chloro-3-(phenoxymethyl)phenyl)-6,6-bis(hydroxymethyl)-2-Methoxytetrahydro-2H-pyran-3,4,5-triol (8.0 g, 18.16 mmol) in DCM (45 mL) under nitrogen atmosphere was added TFA (4.17 mL, 54.4 mmol) at 0° C. The reaction mixture was warmed to r.t. and stirred for 3-4 h. After the completion of the reaction as confirmed by TLC, the reaction mixture was quenched with saturated solution of sodium bicarbonate. The crude compound was extracted with DCM (100 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo to afford crude title compound (7.45 g, 100%) as a white solid which was used without further purification for the next step.

Workup

  1. customAfter the completion of the reaction
  2. customthe reaction mixture was quenched with saturated solution of sodium bicarbonate
  3. extractionThe crude compound was extracted with DCM (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-418ece21fec64a25b880edd121d6027d
Source dataset
uspto-grants-2015_04
Patent number
US09018249B2

Reaction notes

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