2-Hydroxyisobutyric acid → 1-Carboxy-1-methylethyl [(3,4-dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetate

HRID 867997Notes

Reaction equation

HRID 867997 reaction equation
[Cl:1][C:2]1[C:3]([O:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:4][C:5]2[CH2:6][CH2:7][C:8]3([CH2:18][CH2:19][CH3:20])[C:13]([C:14]=2[C:15]=1[Cl:16])=[CH:12][C:11](=[O:17])[CH2:10][CH2:9]3.C(N1C=CN=C1)(N1C=CN=C1)=O.O[C:39]([CH3:44])([CH3:43])[C:40]([OH:42])=[O:41]>O1CCCC1>[Cl:1][C:2]1[C:3]([O:21][CH2:22][C:23]([O:25][C:39]([C:40]([OH:42])=[O:41])([CH3:44])[CH3:43])=[O:24])=[CH:4][C:5]2[CH2:6][CH2:7][C:8]3([CH2:18][CH2:19][CH3:20])[C:13]([C:14]=2[C:15]=1[Cl:16])=[CH:12][C:11](=[O:17])[CH2:10][CH2:9]3

Participants

5

Reactant 3

HCID 116712-Hydroxyisobutyric acidHCID 682631,1'-CarbonyldiimidazoleHCID 21289572[(3,4-Dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetic acid

Product 1

HCID 572896441-Carboxy-1-methylethyl [(3,4-dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(+)[(3,4-Dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetic acid (351 mg, 1 mmole) is dissolved in tetrahydrofuran (10 ml) and treated with 1,1'-carbonyldiimidazole (160 mg, 1 mmole) and the mixture stirred at room temperature for an hour. 2-Hydroxy-2-methylpropionic acid (105 mg, 1 mmole) is added and the mixture stirred for 18 hours at room temperature. The solvent is removed by evaporation in vacuo and the residue purified by column chromatography on silica gel using dichloromethane/tetrahydrofuran/acetic acid (100/2/1, v.v.v.) to give 1-carboxy-1-methylethyl (+)[(3,4-dichloro-6,7,8,8a,9,10-hexahydro-6-oxo-8a-propyl-2-phenanthrenyl)oxy]acetate.

Workup

  1. stirringthe mixture stirred for 18 hours at room temperature
  2. customThe solvent is removed by evaporation in vacuo
  3. customthe residue purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e11c329d387841beb29ac0f1c5004d42
Source dataset
uspto-grants-1988_10
Patent number
US04777281

Reaction notes

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