2-Hydroxyisobutyric acid → HCID 70502486, compound

HRID 358280Notes

Reaction equation

HRID 358280 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[O:19][CH2:20][CH2:21][CH2:22][C:23](N1C=CN=C1)=[O:24].[OH:30][C:31]([CH3:36])([CH3:35])[C:32]([OH:34])=[O:33].[H-].[Na+]>>[Cl:1][C:2]1[C:10]([Cl:11])=[C:9]2[C:5]([CH2:6][C:7]([CH:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)([CH3:13])[C:8]2=[O:12])=[CH:4][C:3]=1[O:19][CH2:20][CH2:21][CH2:22][C:23]([O:30][C:31]([C:32]([OH:34])=[O:33])([CH3:36])[CH3:35])=[O:24]

Participants

4

Reactant 3

HCID 116712-Hydroxyisobutyric acidHCID 24758Sodium hydrideHCID 20449799HCID 20449799, compound

Product 1

HCID 70502486HCID 70502486, compound

Procedure

To the solution of 1-{(+) 4-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]butanoyl}imidazole (0.002 mole) prepared in Step A at 0° C. is added with stirring 2-hydroxyisobutyric acid (0.21 g., 0.002 mole) and a catalytic amount of sodium hydride (10 mg). After stirring overnight at the ambient temperature, the colorless reaction mixture is concentrated in vacuo at 50° C. The resultant yellow liquid is chromatographed using a silica-gel (60 gm) column and eluted with a mixture of methylene chloride, tetrahydrofuran and acetic acid (100/2/1 v.v.v) to give analytically pure 1-carboxy-1-methylethyl (+) 4-[(6,7-dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)oxy]butanoate.

Workup

  1. concentrationthe colorless reaction mixture is concentrated in vacuo at 50° C
  2. customThe resultant yellow liquid is chromatographed
  3. washeluted with a mixture of methylene chloride, tetrahydrofuran and acetic acid (100/2/1 v.v.v)

Sources & evidence

ORD record
ord-10b87ff2d4da497db33df6d1aa85fb8b
Source dataset
uspto-grants-1984_08
Patent number
US04465850

Reaction notes

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