Monobasic potassium phosphate → 7-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanoic acid

HRID 1443650노트

반응식

HRID 1443650 반응식
Cl[O-].[Na+].[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH:23]=[O:24])[S:15][CH:16]=2)=[CH:8][CH:7]=1.P([O-])(O)(O)=[O:26].[K+]>C(O)(C)(C)C.O.C(OCC)(=O)C>[CH3:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:13]=[C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:26])=[O:24])[S:15][CH:16]=2)=[CH:10][CH:11]=1

참가 물질

7

반응물 3

HCID 516951Monobasic potassium phosphateHCID 23665760Sodium HypochloriteHCID 593240777-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanal

생성물 1

HCID 593240787-[4-(4-Methoxyphenyl)thiazol-2-yl]heptanoic acid수율 92.4%

시약·촉매·용매 3

HCID 962Water용매HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매

실험 절차

Add 2-methyl-27-butene (7.0 mL) and sodium hypochlorite (2.51 g, 27.75 mmol) to a solution of 7-[4-(4-methoxyphenyl)thiazol-2-yl]heptanal (4.02 g, 13.25 mmol) and potassium dihydrogen phosphate (3.10 g, 22.78 mmol) in tert-butanol (60 mL) and water (12 mL) at room temperature. Stir the mixture for 40 minutes, dilute with ethyl acetate (500 mL) and wash with brine (3×200 mL). Dry the combined organic extracts over sodium sulfate and remove the solvent under reduced pressure. Purify the residue by flash column chromatography on silica gel, eluting with methanol/methylene chloride (1:19), and triturate the residue with hexanes/methylene chloride to afford 7-[4-(4-methoxyphenyl)thiazol-2-yl]heptanoic acid (3.91 g, 88%): APCI MS m/z 320 [C17H21NO3S+H]+.

후처리

  1. washwash with brine (3×200 mL)
  2. dry with materialDry the combined organic extracts over sodium sulfate
  3. customremove the solvent under reduced pressure
  4. customPurify the residue by flash column chromatography on silica gel
  5. washeluting with methanol/methylene chloride (1:19)
  6. customtriturate the residue with hexanes/methylene chloride

출처 및 근거

ORD 기록
ord-e1866ce6c2e84914a47d010d14876ffa
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07662771B2

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