Methyl bromoacetate → HCID 59596841, compound

HRID 1261443Notes

Reaction equation

HRID 1261443 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:25]=[CH:26][CH:27]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:9][C:8]=1[O:23][CH3:24].C(N(C(C)C)CC)(C)C.[CH3:37][O:38][C:39](=[O:42])[CH2:40]Br>C(#N)C>[CH3:37][O:38][C:39](=[O:42])[CH2:40][N:15]([CH2:14][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]2[CH:25]=[CH:26][CH:27]=[C:2]([F:1])[CH:3]=2)=[C:8]([O:23][CH3:24])[CH:9]=1)[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 59596857HCID 59596857, compound

Product 1

HCID 59596841HCID 59596841, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

1.7 g (4.65 mmol) of [2-[4-(3-fluoro-benzyloxy)-3-methoxy-phenyl]-ethyl]-benzylamine, 1.74 ml (10 mmol) of di-isopropylethylamine and 0.5 ml (5.11 mmol) of 2-bromo-acetic acid methyl ester were dissolved in 20 ml of acetonitrile and the reaction was stirred at 70° C. overnight. The solvent was removed under reduced pressure, water was added to the residue and the product was extracted with ethyl acetate. The crude product was purified by flash chromatography (hexane/ethyl acetate 100:0→80:20 gradient v:v) and 1.94 g (95% yield) of the title compound were isolated as a yellow oil.

Workup

  1. customThe solvent was removed under reduced pressure, water
  2. additionwas added to the residue
  3. extractionthe product was extracted with ethyl acetate
  4. customThe crude product was purified by flash chromatography (hexane/ethyl acetate 100:0→80:20 gradient v:v)

Sources & evidence

ORD record
ord-2408704e029f4f43a6cb50fd5e511365
Source dataset
uspto-grants-2013_06
Patent number
US08470877B2

Reaction notes

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