Water → HCID 53821831, compound

HRID 564936Notes

Reaction equation

HRID 564936 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:23]=[CH:22][C:14]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:24][O:25][CH2:26][CH2:27]Br.O>CN(C)C=O>[C:3]([O:7][C:8]([N:10]([C:11]1[CH:12]=[CH:13][C:14]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:22][CH:23]=1)[CH2:27][CH2:26][O:25][CH3:24])=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 53673833Ethyl 3-[4-[[(1,1-dimethylethoxy)carbonyl]amino]phenyl]-2-propenoate

Product 1

HCID 53821831HCID 53821831, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 165 mg) in N,N-dimethylformamide (1 ml) was added dropwise a solution of ethyl 4-(tert-butoxycarbonylamino)cinnamate (1.00 g) in N,N-dimethylformamide (5 ml) in ice water bath under nitrogen and stirred for 1 hour under same condition. To the mixture was added 2-bromoethyl methyl ether (602 mg) and stirred for 1 hour at same condition and at ambient temperature for 20 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting to a mixture of n-hexane and ethyl acetate (4:1) to give ethyl 4-[N-tert-butoxycarbonyl-N-(2-methoxyethyl)amino]cinnamate (935 mg) as an oil.

Workup

  1. stirringstirred for 1 hour at same condition and at ambient temperature for 20 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel eluting to a mixture of n-hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-35959bb9b1f846c8a19e113cd1f8089d
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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