Water → 1,1-Dimethylethyl 2-(4-(4-fluorophenyl)-1-piperazinyl)-2-oxo-1-(phenylmethyl)ethylcarbamate

HRID 1584758Notes

Reaction equation

HRID 1584758 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[N+](C1C=CC([O:32][C:33](=O)[C@H:34]([CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=CC=1)([O-])=O.O>CN(C)C=O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:33](=[O:32])[CH:34]([NH:35][C:36](=[O:37])[O:38][C:39]([CH3:40])([CH3:41])[CH3:42])[CH2:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 111308Boc-Phe-ONpHCID 162119161-(4-Fluorophenyl)piperazine dihydrochloride

Product 1

HCID 538047351,1-Dimethylethyl 2-(4-(4-fluorophenyl)-1-piperazinyl)-2-oxo-1-(phenylmethyl)ethylcarbamateYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-fluorophenyl)piperazine dihydrochloride (2.53 g, 10 mmol) in N,N-dimethylformamide (40 ml) were added triethylamine (2.8 ml, 20 mmol) and N-tert-butoxycarbonylphenylalanine p-nitrophenyl ester (2.65 g, 10 mmol) in the order mentioned and the mixture was stirred at room temperature overnight. This reaction mixture was poured into cold water and extracted with ethyl acetate. The extract was washed with 1% aqueous ammonia, saturated saline, 0.1N-hydrochloric acid, saturated saline, saturated aqueous sodium hydrogen carbonate solution, and saturated saline in the order mentioned and the organic layer was dried over anhydrous magnesium sulfate and further concentrated under reduced pressure. The residue was purified by silica gel column chromatography using chloroform-methanol (50:1) to provide 1,1-dimethylethyl 2-(4-(4-fluorophenyl)-1-piperazinyl)-2-oxo-1-(phenylmethyl)ethylcarbamate (2.7 g, 92.2%) as colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 1% aqueous ammonia, saturated saline, 0.1N-hydrochloric acid, saturated saline, saturated aqueous sodium hydrogen carbonate solution, and saturated saline in the order
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationfurther concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7399c94bf60d46a6832e0fbc9c260721
Source dataset
uspto-grants-1999_08
Patent number
US05935959

Reaction notes

Loading…