Ethylene Glycol → HCID 86638998, compound

HRID 656229Notes

Reaction equation

HRID 656229 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH:13]([S:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](=[O:24])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:25](O)[CH2:26][OH:27].B(F)(F)F.C(OCC)(=O)C.C1CCCCC1>ClCCl>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:10][CH2:11][C:12]2([O:27][CH2:26][CH2:25][O:24]2)[C@H:13]([S:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6356Boron trifluorideHCID 21867204Cyclohexane ethylacetateHCID 86638995HCID 86638995, compound

Product 1

HCID 86638998HCID 86638998, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the compound of Example 35 Step A (2.00 g, 5.72 mmol), 1,2-ethandiol (2.0 ml, 35.8 mmol), 25 ml of dichloromethane and BF3 (48% purity, 0.60 ml, 4.25 mmol) was stirred for 2 days. The mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate and brine, dried and stripped of the solvent. After chromatography (silica, ethyl acetate/cyclohexane=1/9->15/85) the title compound (toluene/ethyl acetate=9/1, Rf=0.28, 632 mg, 28% yield) was obtained as foam.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. customdried

Sources & evidence

ORD record
ord-2b494487918f485ebfb93545158c3b75
Source dataset
uspto-grants-2011_12
Patent number
US08071643B2

Reaction notes

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