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

HRID 1039154노트

반응식

HRID 1039154 반응식
[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

참가 물질

6

반응물 3

HCID 11205Carbon tetrabromide2회HCID 11776Triphenylphosphine2회HCID 59167774HCID 59167774, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-3ae180d21ed1473a93b9e77a7250a9ab
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552039B2

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