N,N,N',N'-Tetramethylazodicarboxamide → HCID 178418876, 화합물

HRID 10563

반응식

HRID 10563 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N(C(N(C)C)=O)=NC(N(C)C)=O.[C:28](O)(=[O:37])[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1.C(P(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:10][CH2:11][C@H:12]([O:15][C:28](=[O:37])[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 74784-Methoxybenzoic AcidHCID 13831TributylphosphineHCID 178418329HCID 178418329, 화합물

생성물 1

HCID 178418876HCID 178418876, 화합물수율 96.3%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

A solution of Intermediate 35 (21.06 g), 1,1′-azobis(N,N-dimethylformamide) (64.11 g) and p-anisic acid (23.03 g, Tokyo Kasei Kogyo) in tetrahydrofuran (400 ml) was added with tri(n-butyl)phosphine (35.6 ml) at room temperature and stirred at 50° C. for 2.5 hours. The reaction mixture was cooled to room temperature, then added with ethyl acetate (200 ml) and successively washed with saturated aqueous sodium hydrogencarbonate twice (200 ml each) and 0.1 N aqueous sodium hydroxide (50 ml), and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to obtain the title compound (32.92 g).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washsuccessively washed with saturated aqueous sodium hydrogencarbonate twice (200 ml each) and 0.1 N aqueous sodium hydroxide (50 ml)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-6de56dfb6df84ba996ea22062f1fd467
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094789B2

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