Water → HCID 69076582, compound

HRID 1510232Notes

Reaction equation

HRID 1510232 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[C@@H:10]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[NH2:11])=[CH:4][CH:3]=1.[O:20]([CH2:24][CH2:25]Br)[CH2:21][CH2:22]Br.C(N(C(C)C)CC)(C)C.O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[C@H:10]([N:11]2[CH2:25][CH2:24][O:20][CH2:21][CH2:22]2)[CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 28195587HCID 28195587, compound

Product 1

HCID 69076582HCID 69076582, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of N-(4-bromophenyl)-D-phenylalaninamide (500 mg) in N,N-dimethylformamide (5 mL) were added 1,1′-oxybis(2-bromoethane) (545 mg) and diisopropylethylamine (607 mg) and the mixture was stirred at 50° C. for 6 hours. After being cooled to 5° C., the mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford (2R)—N-(4-bromophenyl)-2-morpholin-4-yl-3-phenylpropanamide (430 mg) as a powder.

Workup

  1. temperatureAfter being cooled to 5° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-f8cd037f34ba4175adb3f6451c16fd83
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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