Acetyl chloride → Methyl 2-acetamido-4-(4-octylphenyl)butyrate

HRID 635460Notes

Reaction equation

HRID 635460 reaction equation
Cl.[NH2:2][CH:3]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][CH:11]=1)[C:4]([O:6][CH3:7])=[O:5].[C:24](Cl)(=[O:26])[CH3:25]>C(Cl)Cl.C(N(CC)CC)C>[C:24]([NH:2][CH:3]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][CH:11]=1)[C:4]([O:6][CH3:7])=[O:5])(=[O:26])[CH3:25]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 22618877Methyl 2-amino-4-(4-octylphenyl)butyrate hydrochloride

Product 1

HCID 22618836Methyl 2-acetamido-4-(4-octylphenyl)butyrate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of methyl 2-amino-4-(4-octylphenyl)butyrate hydrochloride (16 g) in methylene chloride (300 ml), triethylamine (16 ml) and acetyl chloride (3.8 ml) were added and the mixture was stirred at room temperature for an hour. Then, methylene chloride (500 ml) was further added to the mixture, the whole mixture was washed with a dilute hydrochloric acid, an aqueous sodium hydrogencarbonate solution and a saturated brine in order and dried over magnesium sulfate. The solvent was distilled away under reduced pressure and the residue was purified by silica gel chromatography (eluent; hexane-ethyl acetate=1:2) to give the subject compound (11 g). MS: 348(M++1).

Workup

  1. washthe whole mixture was washed with a dilute hydrochloric acid
  2. dry with materialan aqueous sodium hydrogencarbonate solution and a saturated brine in order and dried over magnesium sulfate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe residue was purified by silica gel chromatography (eluent; hexane-ethyl acetate=1:2)

Sources & evidence

ORD record
ord-b3e52e11aa774fe0b8567c2aaf55cee6
Source dataset
uspto-grants-2001_02
Patent number
US06187821B1

Reaction notes

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