Ethyl bromoacetate → HCID 86755261, compound

HRID 1953532Notes

Reaction equation

HRID 1953532 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[C:23](=[O:34])/[CH:24]=[CH:25]/[C:26]3[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][CH:27]=3)=[CH:4][C:3]=2[O:2]1.C([O-])([O-])=O.[K+].[K+].[CH2:41]([O:43][C:44](=[O:47])[CH2:45]Br)[CH3:42].C(Cl)Cl.CO>CN(C=O)C>[O:34]=[C:23]([N:11]1[CH2:12][CH2:13][C:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:21][C:22]=2[CH:10]1[C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)/[CH:24]=[CH:25]/[C:26]1[CH:27]=[CH:28][C:29]([CH2:32][O:33][CH2:45][C:44]([O:43][CH2:41][CH3:42])=[O:47])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 21226129Dichloromethane methanolHCID 66993325HCID 66993325, compound

Product 1

HCID 86755261HCID 86755261, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 39 (0.7 g, 1.5 mmol) in 50 mL of DMF was added K2CO3 (0.25 g, 1.2 equiv.) and ethylbromoacetate (0.2 mL, 1.1 equiv.). The resulting mixture was heated at 60° C. for 16 hours until disappearance of the starting material (tlc monitoring, DCM:MeOH (95:5)). A new compound was formed (Rf=0.8). After evaporation of DMF, the residue was taken up in 150 mL of DCM, washed with 2×50 mL of water, dried over Na2SO4 and purified via radial chromatography with DCM to give the title compound (0.85 g, 11%) as a white powder.

Workup

  1. customA new compound was formed (Rf=0.8)
  2. customAfter evaporation of DMF
  3. washwashed with 2×50 mL of water
  4. dry with materialdried over Na2SO4
  5. custompurified via radial chromatography with DCM

Sources & evidence

ORD record
ord-5c49506f87a94c00b28cbc8ef7f83bb7
Source dataset
uspto-grants-2000_09
Patent number
US06117881

Reaction notes

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