Diethyl Ether → Methyl (2RS)-2-(2-oxo-2-phenylethyl)aminoisovalerate

HRID 1061671Notes

Reaction equation

HRID 1061671 reaction equation
C(N(C(C)C)CC)(C)C.Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:13].Cl.[CH3:21][O:22][C:23](=[O:29])[CH:24]([CH:26]([CH3:28])[CH3:27])[NH2:25].C(OCC)C>C(Cl)Cl>[O:13]=[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:11][NH:25][CH:24]([CH:26]([CH3:28])[CH3:27])[C:23]([O:22][CH3:21])=[O:29]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6259Phenacyl bromideHCID 81531DiisopropylethylamineHCID 12498813Valine, methyl ester, hydrochloride (1:1)

Product 1

HCID 21302844Methyl (2RS)-2-(2-oxo-2-phenylethyl)aminoisovalerate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine (7.66 ml) and 2-bromoacetophenone (4.2 g) are added to a suspension of DL-valine methyl ester hydrochloride (3.36 g, Reference compound No. 45-1) in methylene chloride (100 ml), and the mixture is refluxed for four days. The reaction mixture is allowed to stand at room temperature, diethyl ether is added to the mixture, and the whole is extracted with 0.1 N hydrochloric acid. Sodium hydrogencarbonate is added to the extract to basify the system, and the whole is extracted with ethyl acetate. The organic layer is washed with saturated brine and dried over magnesium sulfate. The organic layer is concentrated under reduced pressure to give the titled reference compound (4.92 g).

Workup

  1. customto stand at room temperature
  2. extractionthe whole is extracted with 0.1 N hydrochloric acid
  3. additionSodium hydrogencarbonate is added to the
  4. extractionextract
  5. extractionthe whole is extracted with ethyl acetate
  6. washThe organic layer is washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe organic layer is concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b21c62d70184fe186f3a0b60b0f5822
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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