Triethylamine → 1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-4-methyl-3(2-thienylmethyl)benzene

HRID 1625737Notes

Reaction equation

HRID 1625737 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH2:31][C:32]2[S:33][C:34](Cl)=[CH:35][CH:36]=2)[CH:25]=1)(=[O:3])[CH3:2].C(N(CC)CC)C>O1CCCC1.CO.[C].[Pd]>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@H:6]1[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH2:31][C:32]2[S:33][CH:34]=[CH:35][CH:36]=2)[CH:25]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 8471TriethylamineHCID 666076841-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-3-(5-chloro-2-thienylmethyl)-4-methylbenzene

Product 1

HCID 666079831-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-4-methyl-3(2-thienylmethyl)benzeneYield 69.2%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-(5-chloro-2-thienylmethyl)-4-methylbenzene 57 (12.0 g) obtained in Example 120-(1) was dissolved in tetrahydrofuran (120 ml) and methanol (360 ml), and added thereto were triethylamine (24.2 ml) and 10% palladium carbon catalyst (wet, 3.6 g), and the mixture was stirred at room temperature for 18 hours under hydrogen atmosphere under normal pressure. The insoluble materials were filtered off, washed with tetrahydrofuran, and the filtrate was evaporated under reduced pressure. The residue was dissolved in chloroform, washed successively with a 5% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution and water, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol to give 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-methyl-3(2-thienylmethyl)benzene (7.79 g) as colorless crystals. APCI-Mass m/Z 536 (M+NH4).

Workup

  1. filtrationThe insoluble materials were filtered off
  2. washwashed with tetrahydrofuran
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed successively with a 5% aqueous citric acid solution
  6. dry with materiala saturated aqueous sodium hydrogen carbonate solution and water, and dried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-3e2d1a955244458f85e606e77661cfda
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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