Water → HCID 67774815, 화합물

HRID 1963077노트

반응식

HRID 1963077 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([N+]([O-])=O)=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]=1[CH3:20].[N+:21]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])#[C-:22].C1CCN2C(=NCCC2)CC1.O>C1COCC1.CC(=O)OCC>[CH2:27]([O:26][C:24]([C:23]1[NH:21][CH:22]=[C:9]([CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=2[CH3:20])[C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:25])[CH3:28]

참가 물질

7

반응물 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 533707Ethyl isocyanoacetateHCID 67773638HCID 67773638, 화합물

생성물 1

HCID 67774815HCID 67774815, 화합물수율 62.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

The compound of step 3 (21.45 g, 79.07 mmol) and ethyl isocyanoacetate (10.37 ml, 94.88 mmol) were dissolved in 225 ml of anhydrous THF under a nitrogen atmosphere at 5° C. and DBU (14.16 ml, 94.88 mmol) was added dropwise. The solution was stirred at room temperature for 18 h. Then 200 ml of water and 200 ml of EA were added. The organic phase was washed with 1 N hydrochloric acid (200 ml) and brine (150 ml), dried over magnesium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane/EA, 90:10, then 85:15) to give 16.68 g of the title compound as a yellow solid melting at 120-122° C.

후처리

  1. washThe organic phase was washed with 1 N hydrochloric acid (200 ml) and brine (150 ml)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (cyclohexane/EA, 90:10

출처 및 근거

ORD 기록
ord-7ba9d58585bd4620a8d29bc6c08b9473
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415336B2

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