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Citric Acid → (+/-)-6-{[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid methyl ester

HRID 1926932
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HRID 1926932 반응식
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([OH:10])[CH3:9].Cl[C:13]1[C:14]2[C:21]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[CH:24][CH:23]=3)=[C:20]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:19][C:15]=2[N:16]=[CH:17][N:18]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.O>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([O:10][C:13]1[C:14]2[C:21]([C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=3)=[C:20]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[O:19][C:15]=2[N:16]=[CH:17][N:18]=1)[CH3:9]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 311Citric AcidHCID 13085553Methyl 6-hydroxyheptanoateHCID 580168974-Chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine

생성물 1

HCID 58016791(+/-)-6-{[5-(4-Ethylphenyl)-6-phenylfuro[2,3-d]pyrimidin-4-yl]oxy}heptanoic acid methyl ester

시약·촉매·용매 2

HCID 962Water용매
HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

Put 717 mg (4.48 mmol) (+/−)-6-hydroxyheptanoic acid methyl ester under argon in 10 ml THF and cool to 0° C. Add 2.25 ml (4.48 mmol) of a 2 M solution of phosphazene base P2-tert.-butyl in THF and stir for a further 10 min at RT. Then cool to 0° C. again. Add 1.0 g (2.99 mmol) 4-chloro-5-(4-ethylphenyl)-6-phenylfuro[2,3-d]pyrimidine and continue stirring overnight at RT. Dilute with water, acidify with 10% aqueous citric acid solution and extract twice with ethyl acetate. Combine the ethyl acetate phases and wash once with satd. sodium chloride solution. Dry over magnesium sulphate, concentrate by evaporation and purify the residue by column chromatography on silica gel (solvent: cyclohexane/ethyl acetate 9:1). 640 mg (46.7% of theor.) of the target compound is obtained.

후처리

  1. temperatureThen cool to 0° C. again
  2. stirringcontinue stirring overnight at RT
  3. extractionextract twice with ethyl acetate
  4. washwash once with satd
  5. dry with materialDry over magnesium sulphate
  6. concentrationconcentrate by evaporation
  7. custompurify the residue by column chromatography on silica gel (solvent: cyclohexane/ethyl acetate 9:1)
  8. custom640 mg (46.7% of theor.) of the target compound is obtained

출처 및 근거

ORD 기록
ord-3d7c9415ed9445338bdf1dc3f23e58e6
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183246B2

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