Hydrochloric Acid → (2S,3R,4S,5R,6R)-6-(Acetoxymethyl)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 218985Notes

Reaction equation

HRID 218985 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH2:10][C:11]1[CH:12]=[C:13]([C@@:18]2([O:28][C@H:27]([CH2:29][OH:30])[C@@H:25]([OH:26])[C@H:23]([OH:24])[C@H:21]2[OH:22])[O:19][CH3:20])[CH:14]=[CH:15][C:16]=1[F:17].C(O[C:35](=[O:37])[CH3:36])(=O)C.Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:18]([O:22][C@@H:21]1[C@@H:23]([O:24][C:21](=[O:22])[CH3:23])[C@H:25]([O:26][C:25](=[O:26])[CH3:27])[C@@H:27]([CH2:29][O:30][C:35](=[O:37])[CH3:36])[O:28][C@:18]1([C:13]1[CH:14]=[CH:15][C:16]([F:17])=[C:11]([CH2:10][C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)[CH:12]=1)[O:19][CH3:20])(=[O:19])[CH3:13]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 68587726Methyl 1-C-[3-(benzo[b]thien-2-ylmethyl)-4-fluorophenyl]-alpha-D-glucopyranoside2×

Product 1

HCID 68588258(2S,3R,4S,5R,6R)-6-(Acetoxymethyl)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To the above-obtained toluene solution of methyl 1-C-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-α-glucopyranoside were added pyridine (7.39 g) and 4-dimethylaminopyridine (19 mg). Thereto was added acetic anhydride (7.94 g) at 1.7 to 3.3° C., followed by stirring at room temperature for 12 hours. To the reaction mixture was added hydrochloric acid (2 M, 50 ml), followed by extraction. The organic layer was washed with a 5% aqueous sodium hydrogencarbonate solution (75 ml) and successively with an aqueous sodium chloride solution (25%, 50 ml), and subjected to vacuum distillation to distil off the solvent until the residue became 15 ml, to obtain, as a toluene solution, methyl 2,3,4,6-tetra-O-acetyl-1-C-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-α-glucopyranoside.

Workup

  1. extractionfollowed by extraction
  2. washThe organic layer was washed with a 5% aqueous sodium hydrogencarbonate solution (75 ml) and successively with an aqueous sodium chloride solution (25%, 50 ml)
  3. distillationsubjected to vacuum distillation
  4. customto distil off the solvent until the residue

Sources & evidence

ORD record
ord-9ad3921c7cef484ebcac3e25b418549e
Source dataset
uspto-grants-2012_06
Patent number
US08198464B2

Reaction notes

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