Ethyl Acetate → HCID 53764990, compound

HRID 1033734Notes

Reaction equation

HRID 1033734 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[F:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[C:24]([OH:40])([C:27]([S:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1)([CH3:29])[CH3:28])[CH2:25][OH:26].[C:41]1([C@H:47]([CH3:51])[C:48](O)=[O:49])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.C(OCC)(=O)C>ClCCl>[C:41]1([C@H:47]([CH3:51])[C:48]([O:26][CH2:25][C:24]([C:18]2[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=2[F:16])([OH:40])[C:27]([S:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)([CH3:29])[CH3:28])=[O:49])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10868DicyclohexylcarbodiimideHCID 27246222-Phenylpropionic acid, (+)-HCID 15190126HCID 15190126, compound

Product 1

HCID 53764990HCID 53764990, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 11.7 g (56.7 mmol) of 1,3-dicyclohexylcarbodiimide in 38 ml of dichloromethane was added dropwise to a mixture of 14.0 g (38.0 mmol) of (±)-2-(2,4-difluorophenyl)-3-((4-methoxyphenyl)methylthio)-3-methylbutane-1,2-diol, 6.3 g (41.8 mmol of (S)-(+)-2-phenylpropionic acid, 0.47 g (3.8 mmol) of 4-dimethyl-aminopyridine, and 190 ml of dichloromethane with stirring under ice-cooling, followed by stirring for 3 hours. The mixture was warmed to room temperature, and the stirring was continued for 12 hours. Ethyl acetate was added to the reaction mixture, and the precipitated insoluble matter was removed by filtration. The filtrate was washed successively with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution, and dried. The solvent was removed by distillation under reduced pressure, and the residue was purified by column chromatography using a mixed solvent of hexane and ethyl acetate (10:1) as an eluent. The solvent was removed from each fraction by distillation under reduced pressure to obtain diastereomers (A-1) and (A-2) of 2-(2,4-difluoro-phenyl)-2-hydroxy-3-((4-methoxyphenyl)methylthio)-3-methylbutyl (S)-(+)-2-phenylpropionate in a yield of 9.3 g (49%) and 8.7 g (46%), respectively, as a colorless oily substance.

Workup

  1. temperaturecooling
  2. stirringby stirring for 3 hours
  3. customthe precipitated insoluble matter was removed by filtration
  4. washThe filtrate was washed successively with a saturated sodium hydrogencarbonate aqueous solution
  5. dry with materiala saturated sodium chloride aqueous solution, and dried
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe residue was purified by column chromatography
  8. customThe solvent was removed from each fraction by distillation under reduced pressure

Sources & evidence

ORD record
ord-6f672bce3cae4628b1d78adb237359a6
Source dataset
uspto-grants-1994_05
Patent number
US05312815

Reaction notes

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