Trifluoroacetic acid → 4-[3-[4-[(2-Benzothiazolyl)carbonyl]-1-piperidinyl]propoxy]benzoic acid methyl ester

HRID 1736438노트

반응식

HRID 1736438 반응식
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].C(C(O)=O)(F)(F)F.I[CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O.O1CCCC1>[CH3:37][O:36][C:34](=[O:35])[C:33]1[CH:38]=[CH:39][C:30]([O:29][CH2:28][CH2:27][CH2:26][N:15]2[CH2:16][CH2:17][CH:12]([C:10]([C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[O:11])[CH2:13][CH2:14]2)=[CH:31][CH:32]=1

참가 물질

8

반응물 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 152370094-(Benzthiazole-2-carbonyl)piperidineHCID 153374624-(3-Iodopropoxy)benzoic acid, methyl ester

생성물 1

HCID 153374634-[3-[4-[(2-Benzothiazolyl)carbonyl]-1-piperidinyl]propoxy]benzoic acid methyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

Mix (2-benzothiazolyl)(4-piperidinyl)methanone.CF3CO2H (7.08 g, 19.7 mmol), 4-(3-iodopropoxy)benzoic acid, methyl ester (6.50 g, 20.3 mmol), sodium hydrogen carbonate (3.41 g, 40.6 mmol), tetrahydrofuran (100 mL) and water (20 mL). Heat at reflux under an argon atmosphere overnight. Cool to room temperature, dilute with ethyl acetate (150 mL), wash with 10% sodium hydrogen carbonate (50 mL), water (2×50 mL) and saturated sodium chloride (50 mL). Dry (MgSO4), evaporate the solvent in vacuo and triturate with hexane. Collect the solid by filtration and recrystallize (methanol) to give the title compound as a pale yellow solid; mp 108°-109.5° C.

후처리

  1. temperatureHeat
  2. temperatureat reflux under an argon atmosphere overnight
  3. washwash with 10% sodium hydrogen carbonate (50 mL), water (2×50 mL) and saturated sodium chloride (50 mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customtriturate with hexane
  7. customCollect the solid
  8. filtrationby filtration
  9. customrecrystallize (methanol)

출처 및 근거

ORD 기록
ord-9a8767047be04c28a4e00d82727f1936
출처 데이터셋
uspto-grants-1996_07
특허 번호
US05541200

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