Oxalyl chloride → HCID 86611022, compound

HRID 2245912Notes

Reaction equation

HRID 2245912 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:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2([C:45](O)=[O:46])[CH2:44][CH2:43][CH2:42][CH2:41]2)=[CH:35][CH:34]=1.C(Cl)(=O)C(Cl)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[C@@H:20]([O:21][C:22](=[O:24])[CH3:23])[C@H:15]([O:16][C:17](=[O:19])[CH3:18])[C@H:10]2[O:11][C:12](=[O:14])[CH3:13])[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][C:40]2([CH2:45][OH:46])[CH2:44][CH2:43][CH2:42][CH2:41]2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 86611023HCID 86611023, compound

Product 1

HCID 86611022HCID 86611022, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-[4-(1-hydroxycarbonyl-cyclopent-1-yloxy)-benzyl]-benzene (1.50 g) in dichloromethane (7 mL) cooled in an ice-bath is added oxalyl chloride (1 mL). The solution is stirred at ambient temperature for 4 h and then concentrated under reduced pressure. The residue is dissolved in dry tetrahydrofuran (4 mL), cooled in an ice-bath and treated with sodium borohydride (86 mg). The resultant mixture is stirred at room temperature for 16 h. Water is added and the resulting mixture is extracted with ethyl acetate. The combined extracts are dried (Na2SO4), the solvent is removed in vacuo and the residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0→2:1).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue is dissolved in dry tetrahydrofuran (4 mL)
  3. temperaturecooled in an ice-bath
  4. additiontreated with sodium borohydride (86 mg)
  5. stirringThe resultant mixture is stirred at room temperature for 16 h
  6. additionWater is added
  7. extractionthe resulting mixture is extracted with ethyl acetate
  8. dry with materialThe combined extracts are dried (Na2SO4)
  9. customthe solvent is removed in vacuo
  10. customthe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 1:0→2:1)

Sources & evidence

ORD record
ord-15cb6a63330f4628a1c52bcf88e031f4
Source dataset
uspto-grants-2010_03
Patent number
US07683160B2

Reaction notes

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