Glycine methyl ester → HCID 86251955, compound

HRID 1896705Notes

Reaction equation

HRID 1896705 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[S-:12][C:13]#[N:14].[Na+].[CH3:16][O:17][C:18](=[O:21])[CH2:19][NH2:20]>C(O)C>[CH3:16][O:17][C:18](=[O:21])[CH2:19][NH:20][C:13]1[S:12][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)[N:14]=1

Participants

5

Reactant 3

HCID 69221Glycine methyl esterHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 516871Sodium thiocyanate

Product 1

HCID 86251955HCID 86251955, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

14.5 g (66.8 mmol) of 2-bromo-1-(4-fluorophenyl)ethanone and 5.42 g (66.8 mmol) of sodium thiocyanate were stirred in 250 ml of ethanol at 50° C. for 3 h. 5.95 g (66.8 mmol) of aminoacetic acid methyl ester (prepared from its hydrochloride) in 25 ml of ethanol were added, and the reaction mixture was stirred at room temperature for 4 h and allowed to stand overnight. After concentrating, water and ethyl acetate were added to the residue. The organic phase was separated, washed with water, dried and concentrated. Yield: 8.6 g (48%).

Workup

  1. waitto stand overnight
  2. concentrationAfter concentrating
  3. additionwater and ethyl acetate were added to the residue
  4. customThe organic phase was separated
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bbe560b4709e4128a9646ee378d156c7
Source dataset
uspto-grants-2013_08
Patent number
US08518976B2

Reaction notes

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