Dimethylformamide → HCID 59617257, compound

HRID 2276837Notes

Reaction equation

HRID 2276837 reaction equation
CN(C)C=O.Br[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[C:13]1([C@H:23]([NH:25][C@H:26]2[CH2:30][CH2:29][C@@H:28]([C:31]3[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=3)[CH2:27]2)[CH3:24])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:11]([O:10][C:8](=[O:9])[CH2:7][O:37][C:34]1[CH:33]=[CH:32][C:31]([C@@H:28]2[CH2:29][CH2:30][C@H:26]([NH:25][C@@H:23]([C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[CH3:24])[CH2:27]2)=[CH:36][CH:35]=1)[CH3:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 59617435HCID 59617435, compound

Product 1

HCID 59617257HCID 59617257, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen stream, N,N-dimethylformamide (5 mL) and ethyl bromoacetate (0.13 mL, 1.2 mmol) were added to 4-[(1R,3S)-3-{[(1R)-1-(naphthalen-1-yl)ethyl]amino}cyclopentyl]phenol (331 mg, 1.0 mmol) and potassium carbonate (207 mg, 1.5 mmol), and the mixture was stirred overnight at room temperature. Water was added to the reaction solution, followed by extraction with ethyl acetate. After the extracted solution was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue obtained was purified by column chromatography (NH silica; ethyl acetate/hexane: 5/95-8/92) to give the title compound (298 mg, 71%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialAfter the extracted solution was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue obtained
  5. customwas purified by column chromatography (NH silica; ethyl acetate/hexane: 5/95-8/92)

Sources & evidence

ORD record
ord-5e120b5a40a44b03b89f80f938318522
Source dataset
uspto-grants-2015_09
Patent number
US09133140B2

Reaction notes

Loading…