Ethyl bromoacetate → HCID 67496386, compound

HRID 1628341Notes

Reaction equation

HRID 1628341 reaction equation
[NH2:1][C@@H:2]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:3]([NH:5][C:6]1[N:10]([CH3:11])[N:9]=[C:8]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:7]=1)=[O:4].CCN(C(C)C)C(C)C.Br[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38].[Cl-].[NH4+]>CN(C=O)C>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C@H:2]([NH:1][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:3]([NH:5][C:6]2[N:10]([CH3:11])[N:9]=[C:8]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)[CH:7]=2)=[O:4])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 67497334HCID 67497334, compound

Product 1

HCID 67496386HCID 67496386, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

103.1.B (905 mg, 2.65 mmole), 5 ml of DMF and 0.69 ml of DIEA. The reaction mixture was cooled to 0° C., and then ethyl bromoacetate (0.49 g, 2.92 mmole) was added to the mixture. The reaction was stirred at room temperature overnight. After then, the solution was poured into saturated ammonium chloride, and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. After concentration in vacuo, the residue was chromatographed on silica gel to give 103.1.C (552 mg, 49% yield) as orange syrup.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationAfter concentration in vacuo
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-ef2d8949056740e0a47fde76d6e005a8
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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