Acetic Acid → HCID 12015899, 화합물

HRID 397859노트

반응식

HRID 397859 반응식
[C:1]([O:5][C:6](=[O:27])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([CH2:25][CH3:26])[N:13]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:4])([CH3:3])[CH3:2].C(OC(/N=[N:37]/[C:38]([O:40]CC(Cl)(Cl)Cl)=O)=O)C(Cl)(Cl)Cl.C(O)(=O)C.C[Si]([N:54]=C=O)(C)C>C(OCC)C.C1COCC1.O.[Zn]>[C:1]([O:5][C:6](=[O:27])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([NH:37][C:38]([NH2:54])=[O:40])=[C:12]([CH2:25][CH3:26])[N:13]2[CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

9

반응물 4

HCID 176Acetic AcidHCID 70696Trimethylsilyl isocyanateHCID 6183558HCID 6183558, 화합물HCID 12015898tert-butyl 2-(1-benzyl-2-ethyl-1H-indol-4-yloxy)acetate

생성물 1

HCID 12015899HCID 12015899, 화합물수율 69%

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 2.3 g (6.3 mmol) [[2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid tert-butyl ester and 4.8 g (12.6 mmol) bis(2,2,2-trichloroethyl)azodicarboxylate in diethyl ether is stirred for 24 hours at room temperature. The resulting solid is filtered and vacuum dried. This adduct (1 g, 1.3 mmol) is dissolved in 10 mL of THF and treated with zinc (1 g) and glacial acetic acid (0.5 mL). After stirring for 30 minutes at room temperature an excess of trimethylsilylisocyanate in 1 mL of THF is added and stirring is continued at room temperature for 18 hours. The mixture is diluted with water and extracted with ethyl acetate. The organic layer is washed with brine, dried over MgSO4 and concentrated to dryness to give 0.385 g (69% yield) of the subtitled material. Mass spectrum: 423.

후처리

  1. filtrationThe resulting solid is filtered
  2. customvacuum dried
  3. additionis added
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-90d5e1c0073b4d5f871f6a02e2051c2c
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610728B2

반응 노트

불러오는 중…