Triethylamine → HCID 18760490, compound

HRID 432890Notes

Reaction equation

HRID 432890 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10].[CH2:15]([C:17]1([CH2:27][CH3:28])[C:22](=[O:23])[O:21][CH2:20][C:19]([CH3:26])([CH2:24][OH:25])[NH:18]1)[CH3:16]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:27]([C:17]1([CH2:15][CH3:16])[C:22](=[O:23])[O:21][CH2:20][C:19]([CH3:26])([CH2:24][O:25][C:8](=[O:13])[C:9]([CH3:12])([CH3:11])[CH3:10])[NH:18]1)[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 18760486HCID 18760486, compound

Product 1

HCID 18760490HCID 18760490, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.4 ml (0.017 mol) of triethylamine and then 2.15 g 2 (0.018 mol) of pivaloyl chloride are added dropwise to a solution of 3.45 g (0.017 mol) of 3,3-diethyl-5-methyl-5-hydroxymethylmorpholin-2-one and 0.1 g of 4-dimethylaminopyridine in 20 ml dichloromethane at 15° C. After stirring for 20 hours, the precipitated triethylaminehydrochloride is removed by filtration and the filtrate is washed with water, dried over MgSO4 and concentrated by evaporation in a rotary evaporator. The residue is recrystallised from hexane. This gives 3.9 g (77%) of compound (217), m.p. 51-53° C.

Workup

  1. customthe precipitated triethylaminehydrochloride is removed by filtration
  2. washthe filtrate is washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated by evaporation in a rotary evaporator
  5. customThe residue is recrystallised from hexane

Sources & evidence

ORD record
ord-1ab39690c11f4378acd43fd69f2115a7
Source dataset
uspto-grants-2003_12
Patent number
US06664353B2

Reaction notes

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