Acetic Acid → HCID 29012796, compound

HRID 1526399Notes

Reaction equation

HRID 1526399 reaction equation
[CH3:1][CH:2]([CH3:6])[C@@H:3]([NH2:5])[CH3:4].[CH2:7]=[C:8]1[O:12][C:10](=[O:11])[CH2:9]1.C(O)(=O)C.O>CO>[CH3:1][CH:2]([CH3:6])[C@@H:3]([NH:5][C:10](=[O:11])[CH2:9][C:8](=[O:12])[CH3:7])[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 12661DiketeneHCID 69997881,2-Dimethylpropylamine, (S)-

Product 1

HCID 29012796HCID 29012796, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S)-3-methylbutan-2-amine (30 g, >99% ee, Aldrich) in methanol (180 mL) was added dropwise diketene (29 mL) under ice bath, and the mixture was stirred at room temperature for 20 hr. The mixture was neutralized with acetic acid (120 mL) under ice bath, water was added thereto, and the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (56.6 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-e35b34bbd5f543d0bb4512d74caaf341
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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