Carbon tetrabromide → Methyl 7-(5-phenyl-1,3-oxazol-2-yl)heptanoate

HRID 1616540Notes

Reaction equation

HRID 1616540 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:21])[NH:11][CH2:12][C:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[O:21][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 59167774HCID 59167774, compound

Product 1

HCID 59167750Methyl 7-(5-phenyl-1,3-oxazol-2-yl)heptanoateYield 41.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Add a solution of 7-(2-oxo-2-phenylethylcarbamoyl)heptanoic acid methyl ester (7.05 g, 23.1 mmol) and carbon tetrabromide (11.3 g, 34.3 mmol) in methylene chloride over 40 minutes to a mixture of triphenylphosphine (9.0 g, 34.3 mmol) and DMAP (5.51 g, 45.1 mmol) in methylene chloride (500 mL) at room temperature under nitrogen. Stir the mixture for 30 minutes and add additional triphenylphosphine (2.6 g, 9.92 mmol) and carbon tetrabromide (3.35 g, 10.1 mmol). Stir the mixture for an additional 20 minutes, filter through Celite and wash with ethyl acetate (3×100 mL). Remove the solvent under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (70:30), to provide 7-(5-phenyloxazol-2-yl)heptanoic acid methyl ester (2.75 g, 41%).

Workup

  1. stirringStir the mixture for an additional 20 minutes
  2. filtrationfilter through Celite
  3. washwash with ethyl acetate (3×100 mL)
  4. customRemove the solvent under reduced pressure
  5. custompurify the residue by flash column chromatography on silica gel
  6. washeluting with hexanes/ethyl acetate (70:30)

Sources & evidence

ORD record
ord-1cd4d592bb7a4e94a146a4d9ff4e2b18
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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