Acetic Acid → HCID 20148928, compound

HRID 569302Notes

Reaction equation

HRID 569302 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:17][C:18]1[C:30]([Cl:31])=[C:29]([O:32][CH2:33][C:34]([OH:36])=[O:35])[CH:28]=[C:27]2[C:19]=1[C:20]1[C:25]([CH2:37][CH2:38]O)([CH2:26]2)[CH2:24][CH2:23][C:22](=[O:40])[CH:21]=1>O1CCCC1>[C:1]([O:4][CH2:38][CH2:37][C:25]12[CH2:24][CH2:23][C:22](=[O:40])[CH:21]=[C:20]1[C:19]1[C:27](=[CH:28][C:29]([O:32][CH2:33][C:34]([OH:36])=[O:35])=[C:30]([Cl:31])[C:18]=1[Cl:17])[CH2:26]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 14098158HCID 14098158, compound

Product 1

HCID 20148928HCID 20148928, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of dry tetrahydrofuran (50 ml) containing acetic acid (6.6 mg, 11 mMole) is treated with 1,1'-carbonyldiimidazole (178 mg; 11 mMole) and the mixture stirred under anhydrous conditions for 30 minutes. {[5,6-Dichloro-9a-(2-hydroxyethyl)-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-7-yl]oxy}acetic acid (3.71 g, 10 mMole) is added and the mixture stirred for 16 hours. The solvent is removed by evaporation at reduced pressure. The residue is dissolved in methylene chloride, treated with 11 mM of HCl, washed with water, and dried over MgSO4. The solvent is removed by evaporation at reduced pressure to give the desired product which is recrystallized from acetonitrile.

Workup

  1. stirringthe mixture stirred for 16 hours
  2. customThe solvent is removed by evaporation at reduced pressure
  3. dissolutionThe residue is dissolved in methylene chloride
  4. additiontreated with 11 mM of HCl
  5. washwashed with water
  6. dry with materialdried over MgSO4
  7. customThe solvent is removed by evaporation at reduced pressure

Sources & evidence

ORD record
ord-2bbe6679334a4545bbddd3661a507455
Source dataset
uspto-grants-1988_03
Patent number
US04731471

Reaction notes

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