HCID 86615013, 화합물 → 5-(Cyclopropyl-hydroxymethyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester

HRID 1436673노트

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HRID 1436673 반응식
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH2:6]([O:8][C:9](=[O:25])[C:10]1[CH:22]=[C:21]([CH:23]=[O:24])[CH:20]=[C:12]([C:13]([N:15]([CH3:19])[CH2:16][CH2:17][CH3:18])=[O:14])[CH:11]=1)[CH3:7]>C1COCC1>[CH2:6]([O:8][C:9](=[O:25])[C:10]1[CH:22]=[C:21]([CH:23]([CH:1]2[CH2:3][CH2:2]2)[OH:24])[CH:20]=[C:12]([C:13]([N:15]([CH3:19])[CH2:16][CH2:17][CH3:18])=[O:14])[CH:11]=1)[CH3:7]

참가 물질

4

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HCID 86615013HCID 86615013, 화합물HCID 178418630HCID 178418630, 화합물

생성물 1

HCID 688170545-(Cyclopropyl-hydroxymethyl)-N-methyl-N-propyl-isophthalamic acid ethyl ester수율 38%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

Add cyclopropyl magnesium bromide (0.8 M in THF, 1.3 mL, 1.02 mmol) dropwise to a solution of 5-formyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (283 mg, 1.02 mmol) in THF (5 mL) at −10° C. After stirring at 0° C. for 1.5 h, quench the mixture with 5% aqueous ammonium chloride solution while maintaining the temperature below 5° C. Extract with ethyl acetate (3×30 mL), dry (sodium sulfate) concentrate and purify (silica gel chromatography, eluting with ethyl acetate and hexanes) to give the title compound (122 mg, 38%).

후처리

  1. customquench the mixture with 5% aqueous ammonium chloride solution
  2. temperaturewhile maintaining the temperature below 5° C
  3. extractionExtract with ethyl acetate (3×30 mL)
  4. dry with materialdry (sodium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with ethyl acetate and hexanes)

출처 및 근거

ORD 기록
ord-40f54ce3b6214684b0c3b34f78d1cfd2
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618978B2

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