Hydrochloric Acid → HCID 16103482, compound

HRID 646541Notes

Reaction equation

HRID 646541 reaction equation
[CH2:1]([C:7]1[C:8]2[S:19][CH:18]=[CH:17][C:9]=2[S:10][C:11]=1[C:12]([O:14]CC)=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Li+].[OH-].C1COCC1.Cl>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CO>[CH2:1]([C:7]1[C:8]2[S:19][CH:18]=[CH:17][C:9]=2[S:10][C:11]=1[C:12]([OH:14])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 16103450HCID 16103450, compound

Product 1

HCID 16103482HCID 16103482, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent

Procedure

Compound 61 (32.1 g, 0.11 mol) was mixed with LiOH (10% in water, 50 mL), THF (100 mL), MeOH (30 mL) and a catalytic amount (˜20 mg) tetrabutylammonium iodide in a 500 mL flask. This mixture was heated at reflux overnight, allowed to cool to room temperature, and acidified with concentrated HCl. The resultant yellow solid was collected by filtration and washed thoroughly with water. The solid then was heated with hexane (100 mL) allowed to cool to room temperature. After filtration, the solid was collected, dried over vacuum to yield compound 62 as a light yellow powder (28.0 g, 96.7%). Mp: 110.7-112.4° C.

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe resultant yellow solid was collected by filtration
  4. washwashed thoroughly with water
  5. temperatureThe solid then was heated with hexane (100 mL)
  6. temperatureto cool to room temperature
  7. filtrationAfter filtration
  8. customthe solid was collected
  9. customdried over vacuum

Sources & evidence

ORD record
ord-438093de91cc418e968204794c85625b
Source dataset
uspto-grants-2010_04
Patent number
US07705108B2

Reaction notes

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