Methanol → HCID 12344670, compound

HRID 1757387Notes

Reaction equation

HRID 1757387 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].[C:9](OC(=O)C)(=[O:11])[CH3:10].N1C=CC=C[CH:17]=1.CO>CN(C1C=CN=CC=1)C.C(OCC)C>[C:9]([NH:1][CH:2]([CH:3]([CH3:5])[CH3:4])[C:6](=[O:8])[CH3:17])(=[O:11])[CH3:10]

Participants

7

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 6287L-ValineHCID 7918Acetic Anhydride

Product 1

HCID 12344670HCID 12344670, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of L-valine (25.0 g, 0.21 mol), acetic anhydride (60.5 ml, 0.64 mol), pyridine (52 ml 0.64 mol) and DMAP (2.0 g, 16.6 mmol) was heated at reflux overnight. The reaction mixture was allowed to cool to room temperature and methanol added with rapid stirring. The mixture was concentrated under reduced pressure to give an oil which was dissolved in diethyl ether (250 ml). washed with 2M hydrochloric acid (150 ml), saturated aqueous sodium hydrogen carbonate (150 ml) and brine (150 ml), dried over anhydrous magnesium sulphate, filtered and evaporated. Distillation under reduced pressure gave N-acetyl-2-keto-3-amino-4-methylpentane (6.3 g, 19%) as a viscous straw coloured oil (76-78° C. @1.5 mmHg).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto give an oil which
  5. washwashed with 2M hydrochloric acid (150 ml), saturated aqueous sodium hydrogen carbonate (150 ml) and brine (150 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-f4bcda4e1bdb420e8b78fc938ac51c61
Source dataset
uspto-grants-1995_08
Patent number
US05446032

Reaction notes

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