Diisopropylethylamine → HCID 69416705, compound

HRID 2229357Notes

Reaction equation

HRID 2229357 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH:4]([NH2:10])[CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7].CCN(C(C)C)C(C)C.[N:21]1([C:27](Cl)=[O:28])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1>ClCCl>[CH3:1][O:2][C:3](=[O:11])[CH:4]([NH:10][C:27]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)=[O:28])[CH2:5][C:6]([CH3:7])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 23000049Methyl 2-amino-4,4-dimethylpentanoate

Product 1

HCID 69416705HCID 69416705, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-4,4-dimethyl-pentanoic acid methyl ester (5.35 g, 27.4 mmol) was dissolved in 100 mL of dichloromethane. Hunig's base (7.07 g, 54.7 mmol) and 4-morpholinecarbonyl chloride (4.08 g, 27.4 mmol) were added and the reaction was stirred at ambient temperature 16 h. The reaction mixture was concentrated in vacuo and taken up in 150 mL EtOAc. A white precipitate formed and was filtered and washed with EtOAc. EtOAc solutions were combined and washed with 3×50 mL 1 N HCl (aq), 3×50 saturated NaHCO3 (aq), and 1×50 mL brine. The organic layer was dried over Na2SO4, decanted, and concentrated to a white solid (6.33 g). MS, m/z 273=M+1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customA white precipitate formed
  3. filtrationwas filtered
  4. washwashed with EtOAc
  5. washwashed with 3×50 mL 1 N HCl (aq), 3×50 saturated NaHCO3 (aq), and 1×50 mL brine
  6. dry with materialThe organic layer was dried over Na2SO4
  7. customdecanted
  8. concentrationconcentrated to a white solid (6.33 g)

Sources & evidence

ORD record
ord-ed1f0d6f79604da89259ad8ec7b68033
Source dataset
uspto-grants-2002_07
Patent number
US06420364B1

Reaction notes

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