HCID 131732985, compound → HCID 68264829, compound

HRID 2175670Notes

Reaction equation

HRID 2175670 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([C:31]([C:34]2[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH3:42])=[CH:36][CH:35]=2)([F:33])[CH3:32])[CH:25]=1)(=O)C.ClC1C=CC([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=CC=1C(F)CC1C=CC(OCC)=CC=1>CO.C[O-].[Na+]>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([C@@H:6]2[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]2[OH:4])=[CH:25][C:26]=1[C:31]([C:34]1[CH:35]=[CH:36][C:37]([O:40][CH2:41][CH3:42])=[CH:38][CH:39]=1)([F:33])[CH3:32]

Participants

5

Reactant 2

HCID 131732985HCID 131732985, compoundHCID 131732986HCID 131732986, compound

Product 1

HCID 68264829HCID 68264829, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

3.98 g of the 2,3,4,6-tetra-O-acetyl-1-{4-chloro-3-[1-(4-ethyoxyphenyl)-1-fluoroethyl]phenyl}-1-deoxy-β-D-glucopyranose prepared as above was dissolved in 7 ml of anhydrous methanol containing 0.11 g of sodium methoxide, and stirred for 5 hours at room temperature, and then 1 g of dried strongly acidic resin was added, and stirred overnight at room temperature. The resin was removed by filtration, and the resulting filtrate was evaporated to dryness on a rotary evaporator to afford a white solid, which was 1-{4-chloro-3-[(4-ethyoxyphenyl)-1-fluoroethyl]phenyl}-1-deoxy-β-D-glucopyranose. ESI-MS, m/z=441.2 ([M+1]).

Workup

  1. custom1 g of dried strongly acidic resin
  2. additionwas added
  3. stirringstirred overnight at room temperature
  4. customThe resin was removed by filtration
  5. customthe resulting filtrate was evaporated to dryness on a rotary evaporator
  6. customto afford a white solid, which

Sources & evidence

ORD record
ord-2cdce1a1e5d643a59f952e89da1b5893
Source dataset
uspto-grants-2015_06
Patent number
US09062087B2

Reaction notes

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