Methyl 6-amino-6-oxohexanoate → 5-[4-(2-Methoxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

HRID 1616631Notes

Reaction equation

HRID 1616631 reaction equation
Br[CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])=O.[CH3:14][O:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][C:21](=[O:23])[NH2:22]>CO>[CH3:14][O:15][C:16](=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[O:23][C:2]([CH3:13])=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[O:11][CH3:12])[N:22]=1

Participants

4

Reactant 2

HCID 14266897Methyl 6-amino-6-oxohexanoateHCID 219373832-Bromo-1-(2-methoxyphenyl)propan-1-one

Product 1

HCID 591677855-[4-(2-Methoxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 2-Bromo-1-(2-methoxy-phenyl)-propan-1-one (7.25 g, 29.8 mmol) with 5-carbamoyl-pentanoic acid methyl ester (9.5 g, 60.5 mmol) and heat the neat mixture in a sealed vessel at 140-150° C. for about 4 h. Cool the mixture, transfer to a flask using methanol and concentrate. Partition the residue between water and EtOAc. Dry the combined extracts over Na2SO4 and concentrate. Chromatography over silica gel (MeOH/CH2Cl2) allows for recovery of 5-[4-(2-methoxy-phenyl)-5-methyl-oxazol-2-yl]-pentanoic acid methyl ester (3.63 g, 40%). MS (ES): (M+1)+ 304.2 m/z.

Workup

  1. temperatureCool the mixture, transfer to a flask
  2. concentrationconcentrate
  3. customPartition the residue between water and EtOAc
  4. dry with materialDry the combined extracts over Na2SO4
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-cffe129eb23144bdbf844771ae4c22f6
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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