Acetic Acid → HCID 12015899、化合物

HRID 397859ノート

反応式

HRID 397859 の反応式
[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]

参加物

9

反応物 4

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

生成物 1

HCID 12015899HCID 12015899、化合物収率 69%

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-90d5e1c0073b4d5f871f6a02e2051c2c
出典データセット
uspto-grants-2003_08
特許番号
US06610728B2

反応ノート

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