Hydrochloric Acid → HCID 86754412, compound

HRID 1585545Notes

Reaction equation

HRID 1585545 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:6]([N:8]1[C@H:13]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:12][NH:11][C:10](=[O:24])[CH2:9]1)=[O:7].[H-].[Na+].Br[CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].Cl>O1CCCC1.ClCCl.O>[F:29][C:28]([F:31])([F:30])[C:26]1[CH:25]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:32])[F:33])[CH:27]=1)[C:6]([N:8]1[C@H:13]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:12][N:11]([CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:10](=[O:24])[CH2:9]1)=[O:7]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 54276261HCID 54276261, compound

Product 1

HCID 86754412HCID 86754412, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of (5R)-4-[3,5-bis(trifluoromethyl)benzoyl]-5-(1H-indol-3-ylmethyl)piperazin-2-one (2.15 g) in tetrahydrofuran (43 ml) were added successively sodium hydride (60%) (0.37 g) and ethyl bromoacetate (0.56 ml) in a stream of nitrogen. The mixture was stirred for 55 minutes at the same temperature, and water (20 ml) and 0.5N hydrochloric acid (20 ml) were added successively to the mixture. After stirring for 10 minutes, dichloromethane (80 ml) was added into the mixture at room temperature and the organic layer was separated. The organic layer was washed with brine, and dried over magnesium sulfate. After evaporation in vacuo, the residue was purified by column chromatography on silica gel (60 g) eluting with a mixture of dichloromethane-methanol (from 0% to 2% gradient solution) to give (5R)-4-[3,5-bis(trifluoromethyl)benzoyl]-1-(ethoxycarbonylmethyl)-5-(1H-indol-3-ylmethyl)piperazin-2-one (1.20 g) as an amorphous solid.

Workup

  1. additionwere added successively to the mixture
  2. customthe organic layer was separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation in vacuo
  6. customthe residue was purified by column chromatography on silica gel (60 g)
  7. washeluting with a mixture of dichloromethane-methanol (from 0% to 2% gradient solution)

Sources & evidence

ORD record
ord-bb56af3a4fb64b95818618f5a57aa5e5
Source dataset
uspto-grants-1999_08
Patent number
US05939413

Reaction notes

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