2-Hydroxyisobutyric acid → HCID 53668099, compound

HRID 569309Notes

Reaction equation

HRID 569309 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]12[CH2:19][CH2:18][C:17](=[O:20])[CH:16]=[C:15]1[C:14]1[C:9](=[CH:10][C:11]([O:23][CH2:24][C:25]([OH:27])=[O:26])=[C:12]([Cl:22])[C:13]=1[Cl:21])[CH2:8]2)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.O[C:41]([CH3:46])([CH3:45])[C:42]([OH:44])=[O:43]>O1CCCC1>[C:1]([O:4][CH2:5][CH2:6][C:7]12[CH2:19][CH2:18][C:17](=[O:20])[CH:16]=[C:15]1[C:14]1[C:9](=[CH:10][C:11]([O:23][CH2:24][C:25]([O:27][C:41]([C:42]([OH:44])=[O:43])([CH3:46])[CH3:45])=[O:26])=[C:12]([Cl:22])[C:13]=1[Cl:21])[CH2:8]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 116712-Hydroxyisobutyric acidHCID 682631,1'-CarbonyldiimidazoleHCID 20148928HCID 20148928, compound

Product 1

HCID 53668099HCID 53668099, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

{[9a-(Acetoxyethyl)-5,6-dichloro-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-7-yl]oxy}acetic acid (4.13 g, 10 mMole) is dissolved in dry tetrahydrofuran (20 ml). 1,1'-Carbonyldiimidazole (3.2 g, 10 mMole) is added and the mixture stirred at 20° C. for an hour. 2-Hydroxy-2-methylpropionic acid (1.05 g, 10 mMole) is added and the mixture stirred for 18 hours at 20° C. The solvent is removed by evaporation in vacuo. The residue is dissolved in methylene chloride, washed with water and dried over MgSO4. The solvent is removed by evaporation in vacuo and the residue purified by chromatography using a silica gel column with methylene chloride/tetrahydrofuran/acetic acid 100/2/1 (V.V.V.) as the eluent. Selecting the appropriate cuts gave the desired compound upon evaporation of the solvent in vacuo.

Workup

  1. stirringthe mixture stirred for 18 hours at 20° C
  2. customThe solvent is removed by evaporation in vacuo
  3. dissolutionThe residue is dissolved in methylene chloride
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. customThe solvent is removed by evaporation in vacuo
  7. customthe residue purified by chromatography

Sources & evidence

ORD record
ord-127353321aa74dda8d5621238af7e372
Source dataset
uspto-grants-1988_03
Patent number
US04731471

Reaction notes

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