Hydrochloric Acid → HCID 86610218, compound

HRID 2263598Notes

Reaction equation

HRID 2263598 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][O:28]C(=O)C)[C@@H:20]([O:21]C(=O)C)[C@H:15]([O:16]C(=O)C)[C@H:10]2[O:11]C(=O)C)[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]#[C:40][C:41]2([OH:46])[CH2:45][CH2:44][CH2:43][CH2:42]2)=[CH:35][CH:34]=1.[OH-].[Na+].Cl>CO.O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][OH:28])[C@@H:20]([OH:21])[C@H:15]([OH:16])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]#[C:40][C:41]2([OH:46])[CH2:42][CH2:43][CH2:44][CH2:45]2)=[CH:35][CH:34]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86610219HCID 86610219, compound

Product 1

HCID 86610218HCID 86610218, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.73 g 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-[4-(1-hydroxy-cyclopentyl-ethynyl)-benzyl]-benzene in 4 mL methanol and 2 mL tetrahydrofuran is added 5.1 mL of a 1 M solution of sodium hydroxide in water. The reaction solution is stirred at ambient temperature for 1 h and then neutralized with 1 M hydrochloric acid. The solvent is removed and brine is added to the residue. The resulting mixture is extracted with ethyl acetate and the combined organic extracts are washed with water and brine and dried over sodium sulfate. After removal of the solvent in vacuo the product is yielded.

Workup

  1. customThe solvent is removed
  2. additionbrine is added to the residue
  3. extractionThe resulting mixture is extracted with ethyl acetate
  4. washthe combined organic extracts are washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customAfter removal of the solvent in vacuo the product
  7. customis yielded

Sources & evidence

ORD record
ord-a6f8e254535640709136a01bf5f2f5e3
Source dataset
uspto-grants-2010_12
Patent number
US07851602B2

Reaction notes

Loading…