Citric Acid → HCID 21055322, compound

HRID 2215268Notes

Reaction equation

HRID 2215268 reaction equation
[CH2:1]([C@@H:3]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:4][OH:5])[CH3:2].[S:15](Cl)([C:18]1[CH:24]=[CH:23][C:21]([CH3:22])=[CH:20][CH:19]=1)(=[O:17])=[O:16].N1C=CC=CC=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C1C=CN=CC=1.ClCCl>[C:21]1([CH3:22])[CH:23]=[CH:24][C:18]([S:15]([O:5][CH2:4][C@@H:3]([CH2:1][CH3:2])[CH2:6][O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)(=[O:17])=[O:16])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 21055315HCID 21055315, compound

Product 1

HCID 21055322HCID 21055322, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1.34 g (0.0069 mol) of 2-(R)-ethyl-3-benzyloxypropan-1-ol (XVIId-1), 12 ml of dichloromethane, 1.31 g (0.0069 mol) of tosyl chloride and 0.084 g (0.0007 mol) of 4-dimethylaminopyridine are introduced into a round-bottomed flask kept under an inert atmosphere. The mixture is cooled to 0° C. and then 0.89 ml (0.011 mol) of pyridine is added dropwise. After leaving overnight in a refrigerator, the mixture is hydrolyzed using a 10% aqueous citric acid solution. The phases are separated and the aqueous phase is extracted with ethyl ether. The combined organic phases are washed with water and with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (eluent: dichloromethane/cyclohexane=750:25). 1.54 g (0.0044 mol) of the title compound (XVIIId-1) are obtained.

Workup

  1. customAfter leaving overnight in a refrigerator
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted with ethyl ether
  4. washThe combined organic phases are washed with water and with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by flash chromatography on silica gel (eluent: dichloromethane/cyclohexane=750:25)

Sources & evidence

ORD record
ord-d484efe8775944df990a0ca8ad04a03f
Source dataset
uspto-grants-2006_09
Patent number
US07109234B2

Reaction notes

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