Acetyl chloride → HCID 59167781, compound

HRID 1616606Notes

Reaction equation

HRID 1616606 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:19])[N:12]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29]>>[CH3:1][O:2][C:3](=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH:19][C:28](=[O:30])[CH3:29])[N:12]=1

Participants

4

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 59167769HCID 59167769, compound

Product 1

HCID 59167781HCID 59167781, compound

Procedure

Dissolve 5-[4-(2-amino-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (4.05 g, 14.8 mmol) and triethylamine (2.26 mL, 16.2 mmol) in TI-IF (40 mL) and stir at room temperature. Add acetyl chloride (1.16 mL, 16.2 mmol) and allow the mixture to stir overnight at room temperature. Concentrate the mixture and partition the residue between aq NaHCO3 and EtOAc. Dry the combined extracts over Na2SO4 before concentrating. Chromatograph the residue over silica gel (MeOH/CH2Cl2) which allows for the isolation of 5-[4-(2-acetylamino-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (3.51 g, 75%). MS (ES): (M+1)+ 317.2 m/z.

Workup

  1. stirringto stir overnight at room temperature
  2. concentrationConcentrate the mixture
  3. custompartition the residue between aq NaHCO3 and EtOAc
  4. dry with materialDry the combined extracts over Na2SO4
  5. concentrationbefore concentrating

Sources & evidence

ORD record
ord-dd90a6723ef2436ab1abb59faaf9266e
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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