Acetic Acid → HCID 12015899、化合物

HRID 1280816ノート

反応式

HRID 1280816 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 was stirred for 24 hours at room temperature. The resulting solid was filtered and vacuum dried. This adduct (1 g, 1.3 mmol) was 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 was added stirring was continued at room temperature for 18 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was 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 was filtered
  2. customvacuum dried
  3. additionwas added
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-872616fdf8624e3cb302ec74d38e75b9
出典データセット
uspto-grants-2002_09
特許番号
US06451839B1

反応ノート

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