Potassium Carbonate → HCID 57597564, compound

HRID 1786555Notes

Reaction equation

HRID 1786555 reaction equation
Br[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:15]([O:17][C:18]([C@@H:20]1[CH2:24][C@H:23]([NH:25][C:26](=[O:41])[CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:22][NH:21]1)=[O:19])[CH3:16].C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[CH2:15]([O:17][C:18]([C@@H:20]1[CH2:24][C@H:23]([NH:25][C:26](=[O:41])[CH2:27][CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:22][N:21]1[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:19])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 57597565HCID 57597565, compound

Product 1

HCID 57597564HCID 57597564, compoundYield 57.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of bromodiphenylmethane (0.4 g, 1.64 mmol) in butanone (10 ml) was added (2S,4S)-4-(3,3-diphenyl-propionylamino)-pyrrolidine-2-carboxylic acid ethyl ester (36) (0.6 g, 1.64 mmol), K2CO3 (0.23 g, 1.64 mmol) and KI (0.27 g, 1.64 mmol). The mixture was heated under reflux for 18 hours, and then filtered and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2 (50 ml) and washed with water (10 ml). Drying over MgSO4 and removal of solvent under reduced pressure followed by column chromatography using Hex:EtOAc (1:1) gives 0.5 g the desired product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in CH2Cl2 (50 ml)
  6. washwashed with water (10 ml)
  7. dry with materialDrying over MgSO4 and removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-bac9ddbcb8d04a9bba676089661f1a08
Source dataset
uspto-grants-2009_03
Patent number
US07507760B2

Reaction notes

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