Acetyl chloride → HCID 16748200, compound

HRID 2084460Notes

Reaction equation

HRID 2084460 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C@H:8]([CH2:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[O:5][N:4]=1.[C:26](Cl)([CH3:28])=[O:27].C([O-])(O)=O.[Na+]>C1COCC1>[C:26]([NH:1][CH2:2][C:3]1[N:7]=[C:6]([C@H:8]([CH2:17][CH2:18][CH2:19][CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[O:5][N:4]=1)(=[O:27])[CH3:28]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 516892Sodium BicarbonateHCID 16747946tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate

Product 1

HCID 16748200HCID 16748200, compoundYield 101.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl (3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate (preparation 18) (219 mg, 0.62 mmol) in THF (10 ml) was treated with AcCl (53 μl, 0.75 mmol) and stirred at room temperature for 1 hour. More AcCl (200 μl) was added and stirred for a further hour. Sat. NaHCO3 solution was added and the layers separated. The organic extract was washed with brine, dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure to afford the title compound as a colourless oil (247 mg, 100%).

Workup

  1. stirringstirred for a further hour
  2. customthe layers separated
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a66f9ec73bb940ccba3323e534055250
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

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